CA2329316A1 - Main-group metal-based asymmetric catalysts and applications thereof - Google Patents
Main-group metal-based asymmetric catalysts and applications thereof Download PDFInfo
- Publication number
- CA2329316A1 CA2329316A1 CA002329316A CA2329316A CA2329316A1 CA 2329316 A1 CA2329316 A1 CA 2329316A1 CA 002329316 A CA002329316 A CA 002329316A CA 2329316 A CA2329316 A CA 2329316A CA 2329316 A1 CA2329316 A1 CA 2329316A1
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- Canada
- Prior art keywords
- catalyst
- chiral
- independently
- racemic
- nucleophile
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 229910052751 metal Inorganic materials 0.000 title claims abstract description 120
- 239000002184 metal Substances 0.000 title claims abstract description 116
- 239000011982 enantioselective catalyst Substances 0.000 title description 3
- 239000003054 catalyst Substances 0.000 claims abstract description 237
- 238000000034 method Methods 0.000 claims abstract description 151
- 239000003446 ligand Substances 0.000 claims abstract description 128
- 239000000758 substrate Substances 0.000 claims abstract description 91
- 239000012038 nucleophile Substances 0.000 claims abstract description 75
- 238000007792 addition Methods 0.000 claims abstract description 32
- 238000005935 nucleophilic addition reaction Methods 0.000 claims abstract description 24
- 230000000707 stereoselective effect Effects 0.000 claims abstract description 23
- 125000001424 substituent group Chemical group 0.000 claims description 158
- 238000006243 chemical reaction Methods 0.000 claims description 133
- -1 selenoalkyl Chemical class 0.000 claims description 129
- 125000000217 alkyl group Chemical group 0.000 claims description 104
- 150000002466 imines Chemical class 0.000 claims description 99
- 125000000623 heterocyclic group Chemical group 0.000 claims description 96
- 150000001408 amides Chemical class 0.000 claims description 74
- 230000008569 process Effects 0.000 claims description 72
- 150000001299 aldehydes Chemical class 0.000 claims description 71
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 71
- 150000002148 esters Chemical class 0.000 claims description 71
- 150000002576 ketones Chemical class 0.000 claims description 70
- 125000003342 alkenyl group Chemical group 0.000 claims description 68
- 125000004429 atom Chemical group 0.000 claims description 68
- 125000000304 alkynyl group Chemical group 0.000 claims description 67
- 229910052739 hydrogen Inorganic materials 0.000 claims description 67
- 125000003118 aryl group Chemical group 0.000 claims description 62
- 239000001257 hydrogen Substances 0.000 claims description 59
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 58
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 58
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- 229910052736 halogen Inorganic materials 0.000 claims description 52
- 150000002367 halogens Chemical class 0.000 claims description 52
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 52
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- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims description 46
- 150000001412 amines Chemical class 0.000 claims description 46
- 125000003545 alkoxy group Chemical group 0.000 claims description 45
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 39
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 38
- 150000003573 thiols Chemical class 0.000 claims description 36
- 238000006467 substitution reaction Methods 0.000 claims description 33
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 30
- 229910052717 sulfur Inorganic materials 0.000 claims description 30
- 238000003786 synthesis reaction Methods 0.000 claims description 27
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 26
- 150000001875 compounds Chemical class 0.000 claims description 26
- 229910052760 oxygen Inorganic materials 0.000 claims description 25
- 229910052744 lithium Inorganic materials 0.000 claims description 24
- 229910052749 magnesium Inorganic materials 0.000 claims description 24
- 239000000203 mixture Substances 0.000 claims description 24
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 23
- 229910052782 aluminium Inorganic materials 0.000 claims description 23
- 230000015572 biosynthetic process Effects 0.000 claims description 23
- 229910052700 potassium Inorganic materials 0.000 claims description 23
- 229910052708 sodium Inorganic materials 0.000 claims description 23
- 229910052791 calcium Inorganic materials 0.000 claims description 22
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 18
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims description 18
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 18
- 239000001301 oxygen Substances 0.000 claims description 17
- 229910052710 silicon Inorganic materials 0.000 claims description 17
- 229910052725 zinc Inorganic materials 0.000 claims description 17
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 16
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 16
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 16
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- 239000002585 base Substances 0.000 claims description 16
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- 229910052733 gallium Inorganic materials 0.000 claims description 16
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- 239000011593 sulfur Substances 0.000 claims description 16
- 229910052718 tin Inorganic materials 0.000 claims description 16
- 150000001540 azides Chemical class 0.000 claims description 15
- 150000007942 carboxylates Chemical class 0.000 claims description 15
- 229910052701 rubidium Inorganic materials 0.000 claims description 15
- 229910052711 selenium Inorganic materials 0.000 claims description 15
- 239000011669 selenium Substances 0.000 claims description 15
- 229910052712 strontium Inorganic materials 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 14
- 150000004703 alkoxides Chemical class 0.000 claims description 14
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 claims description 14
- 229910052757 nitrogen Inorganic materials 0.000 claims description 14
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 14
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 claims description 13
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- 150000003949 imides Chemical class 0.000 claims description 13
- 150000002923 oximes Chemical class 0.000 claims description 13
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 claims description 13
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 13
- LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical group [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 claims description 13
- 239000007848 Bronsted acid Substances 0.000 claims description 12
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 12
- 239000012948 isocyanate Substances 0.000 claims description 12
- 150000002513 isocyanates Chemical class 0.000 claims description 12
- 239000002879 Lewis base Substances 0.000 claims description 11
- 150000002118 epoxides Chemical class 0.000 claims description 11
- 150000007527 lewis bases Chemical class 0.000 claims description 11
- 230000003197 catalytic effect Effects 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 9
- 125000004001 thioalkyl group Chemical group 0.000 claims description 9
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 claims description 8
- RAABOESOVLLHRU-UHFFFAOYSA-N diazene Chemical group N=N RAABOESOVLLHRU-UHFFFAOYSA-N 0.000 claims description 8
- 229910052698 phosphorus Inorganic materials 0.000 claims description 8
- 239000011574 phosphorus Substances 0.000 claims description 8
- 229910052719 titanium Inorganic materials 0.000 claims description 8
- NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical compound C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 claims description 7
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 claims description 7
- 101100149678 Caenorhabditis elegans snr-3 gene Proteins 0.000 claims description 7
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 7
- GNVMUORYQLCPJZ-UHFFFAOYSA-M Thiocarbamate Chemical compound NC([S-])=O GNVMUORYQLCPJZ-UHFFFAOYSA-M 0.000 claims description 7
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 7
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 7
- 125000004414 alkyl thio group Chemical group 0.000 claims description 7
- 150000001409 amidines Chemical class 0.000 claims description 7
- 150000008064 anhydrides Chemical class 0.000 claims description 7
- 229910052785 arsenic Inorganic materials 0.000 claims description 7
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 claims description 7
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 7
- 229910052796 boron Inorganic materials 0.000 claims description 7
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- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 claims description 7
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 7
- 150000003857 carboxamides Chemical class 0.000 claims description 7
- 229910052802 copper Inorganic materials 0.000 claims description 7
- AEOCXXJPGCBFJA-UHFFFAOYSA-N ethionamide Chemical compound CCC1=CC(C(N)=S)=CC=N1 AEOCXXJPGCBFJA-UHFFFAOYSA-N 0.000 claims description 7
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 7
- 125000001072 heteroaryl group Chemical group 0.000 claims description 7
- 150000007857 hydrazones Chemical class 0.000 claims description 7
- 125000006413 ring segment Chemical group 0.000 claims description 7
- 229910052709 silver Inorganic materials 0.000 claims description 7
- 125000003107 substituted aryl group Chemical group 0.000 claims description 7
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- 125000003441 thioacyl group Chemical group 0.000 claims description 7
- 229910052726 zirconium Inorganic materials 0.000 claims description 7
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 6
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 6
- 125000002252 acyl group Chemical group 0.000 claims description 6
- 150000003951 lactams Chemical class 0.000 claims description 6
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- 238000006735 epoxidation reaction Methods 0.000 claims description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 3
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- 229910052788 barium Inorganic materials 0.000 claims 14
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- 239000002243 precursor Substances 0.000 description 1
- 238000002953 preparative HPLC Methods 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000011514 reflex Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 description 1
- 125000005353 silylalkyl group Chemical group 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 230000009897 systematic effect Effects 0.000 description 1
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 1
- 150000003553 thiiranes Chemical class 0.000 description 1
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 description 1
- 125000000101 thioether group Chemical group 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- 125000005490 tosylate group Chemical group 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/08—Preparation of carboxylic acid nitriles by addition of hydrogen cyanide or salts thereof to unsaturated compounds
- C07C253/10—Preparation of carboxylic acid nitriles by addition of hydrogen cyanide or salts thereof to unsaturated compounds to compounds containing carbon-to-carbon double bonds
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
- B01J31/1805—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing nitrogen
- B01J31/181—Cyclic ligands, including e.g. non-condensed polycyclic ligands, comprising at least one complexing nitrogen atom as ring member, e.g. pyridine
- B01J31/1825—Ligands comprising condensed ring systems, e.g. acridine, carbazole
- B01J31/183—Ligands comprising condensed ring systems, e.g. acridine, carbazole with more than one complexing nitrogen atom, e.g. phenanthroline
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/22—Organic complexes
- B01J31/2204—Organic complexes the ligands containing oxygen or sulfur as complexing atoms
- B01J31/2208—Oxygen, e.g. acetylacetonates
- B01J31/2226—Anionic ligands, i.e. the overall ligand carries at least one formal negative charge
- B01J31/2243—At least one oxygen and one nitrogen atom present as complexing atoms in an at least bidentate or bridging ligand
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B53/00—Asymmetric syntheses
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/30—Preparation of optical isomers
- C07C227/32—Preparation of optical isomers by stereospecific synthesis
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/30—Addition reactions at carbon centres, i.e. to either C-C or C-X multiple bonds
- B01J2231/34—Other additions, e.g. Monsanto-type carbonylations, addition to 1,2-C=X or 1,2-C-X triplebonds, additions to 1,4-C=C-C=X or 1,4-C=-C-X triple bonds with X, e.g. O, S, NH/N
- B01J2231/341—1,2-additions, e.g. aldol or Knoevenagel condensations
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/30—Addition reactions at carbon centres, i.e. to either C-C or C-X multiple bonds
- B01J2231/34—Other additions, e.g. Monsanto-type carbonylations, addition to 1,2-C=X or 1,2-C-X triplebonds, additions to 1,4-C=C-C=X or 1,4-C=-C-X triple bonds with X, e.g. O, S, NH/N
- B01J2231/348—1,4-additions, e.g. conjugate additions
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/02—Compositional aspects of complexes used, e.g. polynuclearity
- B01J2531/0238—Complexes comprising multidentate ligands, i.e. more than 2 ionic or coordinative bonds from the central metal to the ligand, the latter having at least two donor atoms, e.g. N, O, S, P
- B01J2531/0241—Rigid ligands, e.g. extended sp2-carbon frameworks or geminal di- or trisubstitution
- B01J2531/0244—Pincer-type complexes, i.e. consisting of a tridentate skeleton bound to a metal, e.g. by one to three metal-carbon sigma-bonds
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/02—Compositional aspects of complexes used, e.g. polynuclearity
- B01J2531/0238—Complexes comprising multidentate ligands, i.e. more than 2 ionic or coordinative bonds from the central metal to the ligand, the latter having at least two donor atoms, e.g. N, O, S, P
- B01J2531/0241—Rigid ligands, e.g. extended sp2-carbon frameworks or geminal di- or trisubstitution
- B01J2531/025—Ligands with a porphyrin ring system or analogues thereof, e.g. phthalocyanines, corroles
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/02—Compositional aspects of complexes used, e.g. polynuclearity
- B01J2531/0238—Complexes comprising multidentate ligands, i.e. more than 2 ionic or coordinative bonds from the central metal to the ligand, the latter having at least two donor atoms, e.g. N, O, S, P
- B01J2531/0241—Rigid ligands, e.g. extended sp2-carbon frameworks or geminal di- or trisubstitution
- B01J2531/0252—Salen ligands or analogues, e.g. derived from ethylenediamine and salicylaldehyde
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- B—PERFORMING OPERATIONS; TRANSPORTING
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- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/30—Complexes comprising metals of Group III (IIIA or IIIB) as the central metal
- B01J2531/31—Aluminium
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/40—Complexes comprising metals of Group IV (IVA or IVB) as the central metal
- B01J2531/46—Titanium
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/60—Complexes comprising metals of Group VI (VIA or VIB) as the central metal
- B01J2531/62—Chromium
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/70—Complexes comprising metals of Group VII (VIIB) as the central metal
- B01J2531/72—Manganese
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/82—Metals of the platinum group
- B01J2531/821—Ruthenium
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/84—Metals of the iron group
- B01J2531/845—Cobalt
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Toxicology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/071,842 US6521561B1 (en) | 1998-05-01 | 1998-05-01 | Main-group metal based asymmetric catalysts and applications thereof |
| US09/071,842 | 1998-05-01 | ||
| PCT/US1999/009570 WO1999056699A2 (en) | 1998-05-01 | 1999-04-30 | Main-group metal-based asymmetric catalysts and applications thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2329316A1 true CA2329316A1 (en) | 1999-11-11 |
Family
ID=22103940
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002329316A Abandoned CA2329316A1 (en) | 1998-05-01 | 1999-04-30 | Main-group metal-based asymmetric catalysts and applications thereof |
Country Status (5)
| Country | Link |
|---|---|
| US (3) | US6521561B1 (https=) |
| EP (1) | EP1073613A2 (https=) |
| JP (1) | JP2002513734A (https=) |
| CA (1) | CA2329316A1 (https=) |
| WO (1) | WO1999056699A2 (https=) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6562967B2 (en) * | 2000-07-31 | 2003-05-13 | Brandeis University | Kinetic resolutions of chiral 2-and-3-substituted carboxylic acids |
| US6562966B2 (en) * | 2000-07-31 | 2003-05-13 | Brandeis University | Kinetic resolutions of chiral 2- and 3-substituted carboxylic acids |
| US7482483B2 (en) | 2004-01-27 | 2009-01-27 | University Of South Florida | Growth factor-binding compounds and methods of use |
| US7531662B2 (en) | 2003-06-11 | 2009-05-12 | Brandeis University | Cinchona-alkaloid-based catalysts, and asymmetric alcoholysis of cyclic anhydrides using them |
Families Citing this family (53)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100342541B1 (ko) * | 1998-04-16 | 2002-06-28 | 나까니시 히로유끼 | 올레핀 중합촉매 및 중합방법 |
| JP5258077B2 (ja) * | 1999-11-01 | 2013-08-07 | ダブリュー・アール・グレイス・アンド・カンパニー−コネチカット | オレフィン重合用の活性を持った三配座不均一担持触媒 |
| JP4535216B2 (ja) * | 2000-04-12 | 2010-09-01 | 日産化学工業株式会社 | 光学活性コバルト錯体及び不斉シクロプロパン化反応 |
| US6703508B2 (en) | 2000-12-04 | 2004-03-09 | Sepracor, Inc. | Methods for the stereoselective synthesis of substituted piperidines |
| DE60211884T2 (de) | 2001-04-30 | 2006-11-23 | Ciba Speciality Chemicals Holding Inc. | Verwendung von metallkomplexverbindungen als oxidationskatalysatoren |
| US6884750B2 (en) * | 2001-06-27 | 2005-04-26 | Rs Tech Corp. | Chiral salen catalyst and methods for the preparation of chiral compounds from racemic epoxides by using new catalyst |
| US6974665B2 (en) | 2001-09-06 | 2005-12-13 | University Of Nebraska | In situ screening to optimize variables in organic reactions |
| US6864205B2 (en) * | 2001-12-18 | 2005-03-08 | Univation Technologies, Llc | Heterocyclic-amide catalyst compositions for the polymerization of olefins |
| US7199255B2 (en) * | 2001-12-18 | 2007-04-03 | Univation Technologies, Llc | Imino-amide catalysts for olefin polymerization |
| US7001863B2 (en) * | 2001-12-18 | 2006-02-21 | Univation Technologies, Llc | Monoamide based catalyst compositions for the polymerization of olefins |
| GB0209317D0 (en) * | 2002-04-24 | 2002-06-05 | Bp Chem Int Ltd | Polymerisation catalyst |
| DE602004006965T2 (de) | 2003-02-07 | 2008-02-21 | Basell Polyolefine Gmbh | Polymerisationskatalysatoren, organische übergangsmetallverbindungen, verfahren zur herstellung von polyolefinen |
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| CN106317264B (zh) * | 2015-07-01 | 2018-11-30 | 中国石化扬子石油化工有限公司 | 一种用水杨醛亚胺型改性剂改性的负载型MgCl2/TiCl4催化剂及其制备方法和应用 |
| CN107402206B (zh) * | 2017-07-18 | 2020-04-07 | 闽南师范大学 | 一种汞离子比色传感器及其制备方法和应用 |
| JP2021522355A (ja) | 2018-04-18 | 2021-08-30 | サウジ アラムコ テクノロジーズ カンパニー | ポリ（アルキレンカーボネート）ポリマーの末端基異性化 |
| WO2020028606A1 (en) | 2018-08-02 | 2020-02-06 | Saudi Aramco Technologies Company | Sustainable polymer compositions and methods |
| MA53727A (fr) | 2018-09-24 | 2021-12-29 | Saudi Aramco Tech Co | Copolymères séquencés de polycarbonate et procédés associés |
| CN112094215B (zh) * | 2020-11-02 | 2021-09-24 | 浙江工业大学 | 一种一锅法合成3-氨基吡咯烷盐酸盐的方法 |
| US12195576B2 (en) | 2021-06-23 | 2025-01-14 | Saudi Aramco Technologies Company | Polyol compositions and methods |
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| WO1999034788A1 (en) * | 1998-01-09 | 1999-07-15 | Arizona Board Of Regents, A Body Corporate, Acting On Behalf Of Arizona State University | Synthesis of phenstatin and prodrugs thereof |
| US6130340A (en) * | 1998-01-13 | 2000-10-10 | President And Fellows Of Harvard College | Asymmetric cycloaddition reactions |
| US6316616B1 (en) * | 1998-04-02 | 2001-11-13 | President And Fellows Of Harvard College | Parallel combinatorial approach to the discovery and optimization of catalysts and uses thereof |
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- 1999-04-30 CA CA002329316A patent/CA2329316A1/en not_active Abandoned
- 1999-04-30 WO PCT/US1999/009570 patent/WO1999056699A2/en not_active Ceased
- 1999-04-30 EP EP99922765A patent/EP1073613A2/en not_active Withdrawn
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2002
- 2002-12-20 US US10/325,592 patent/US6844448B2/en not_active Expired - Fee Related
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2005
- 2005-01-04 US US11/029,183 patent/US20050209471A1/en not_active Abandoned
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6562967B2 (en) * | 2000-07-31 | 2003-05-13 | Brandeis University | Kinetic resolutions of chiral 2-and-3-substituted carboxylic acids |
| US6562966B2 (en) * | 2000-07-31 | 2003-05-13 | Brandeis University | Kinetic resolutions of chiral 2- and 3-substituted carboxylic acids |
| US6743914B2 (en) | 2000-07-31 | 2004-06-01 | Brandeis University | Kinetic resolutions of chiral 2-and 3-substituted carboxylic acids |
| US7057038B2 (en) | 2000-07-31 | 2006-06-06 | Brandeis University | Kinetic resolutions of chiral 2- and 3-substituted carboxylic acids |
| US7767811B2 (en) | 2000-07-31 | 2010-08-03 | Brandeis University | Kinetic resolutions of chiral 2- and 3-substituted carboxylic acids |
| US7531662B2 (en) | 2003-06-11 | 2009-05-12 | Brandeis University | Cinchona-alkaloid-based catalysts, and asymmetric alcoholysis of cyclic anhydrides using them |
| US7482483B2 (en) | 2004-01-27 | 2009-01-27 | University Of South Florida | Growth factor-binding compounds and methods of use |
| US7718700B2 (en) | 2004-01-27 | 2010-05-18 | Yale University | Growth factor-binding compounds and methods of use |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2002513734A (ja) | 2002-05-14 |
| US6844448B2 (en) | 2005-01-18 |
| US6521561B1 (en) | 2003-02-18 |
| WO1999056699A3 (en) | 2000-05-18 |
| US20030187249A1 (en) | 2003-10-02 |
| WO1999056699A2 (en) | 1999-11-11 |
| EP1073613A2 (en) | 2001-02-07 |
| US20050209471A1 (en) | 2005-09-22 |
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