WO2001000545A1 - PRODUCTION OF OPTICALLY ACTIVE α-HYDROXYACETALS - Google Patents

PRODUCTION OF OPTICALLY ACTIVE α-HYDROXYACETALS Download PDF

Info

Publication number
WO2001000545A1
WO2001000545A1 PCT/EP1999/008446 EP9908446W WO0100545A1 WO 2001000545 A1 WO2001000545 A1 WO 2001000545A1 EP 9908446 W EP9908446 W EP 9908446W WO 0100545 A1 WO0100545 A1 WO 0100545A1
Authority
WO
WIPO (PCT)
Prior art keywords
alkyl
carbon atoms
phenyl
process according
group
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.)
Ceased
Application number
PCT/EP1999/008446
Other languages
English (en)
French (fr)
Inventor
Martin Studer
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Solvias AG
Original Assignee
Solvias AG
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Solvias AG filed Critical Solvias AG
Priority to JP2001506961A priority Critical patent/JP2003503372A/ja
Priority to EP99973927A priority patent/EP1187798B8/en
Priority to US10/018,365 priority patent/US6660890B1/en
Priority to DE69931966T priority patent/DE69931966T2/de
Priority to AU13792/00A priority patent/AU1379200A/en
Publication of WO2001000545A1 publication Critical patent/WO2001000545A1/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • 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
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/48—Preparation of compounds having groups
    • 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

Definitions

  • aromatic radicals in question are especially naphthyl and in particular phenyl.
  • aromatic-aliphatic radicals in question are preferably phenyl- or naphthyl-d-C -alkyl or -C 2 -C 4 -alkenyl.
  • Some examples are benzyl, naphthylmethyl, ⁇ -phenylethyl and ⁇ -phenyl- ethenyl.
  • Hydrogenation is preferably carried out at a hydrogen pressure of up to 200 bar, more preferably up to 150 bar, most preferably 10 to 100 bar.
  • the reaction temperature may be for example -50 to 100°C, more preferably 0 to 50°C, most preferably 0 to 35°C.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Catalysts (AREA)
  • Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
PCT/EP1999/008446 1999-06-23 1999-11-04 PRODUCTION OF OPTICALLY ACTIVE α-HYDROXYACETALS Ceased WO2001000545A1 (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
JP2001506961A JP2003503372A (ja) 1999-06-23 1999-11-04 光学活性α−ヒドロキシアセタールの製造
EP99973927A EP1187798B8 (en) 1999-06-23 1999-11-04 Production of optically active alpha-hydroxyacetals
US10/018,365 US6660890B1 (en) 1999-06-23 1999-11-04 Production of optically active α-hydroxyacetals
DE69931966T DE69931966T2 (de) 1999-06-23 1999-11-04 Herstellung von optisch aktiven alphahydroxyacetalen
AU13792/00A AU1379200A (en) 1999-06-23 1999-11-04 Production of optically active alpha-hydroxyacetals

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH1170/99 1999-06-23
CH117099 1999-06-23

Publications (1)

Publication Number Publication Date
WO2001000545A1 true WO2001000545A1 (en) 2001-01-04

Family

ID=4204129

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1999/008446 Ceased WO2001000545A1 (en) 1999-06-23 1999-11-04 PRODUCTION OF OPTICALLY ACTIVE α-HYDROXYACETALS

Country Status (7)

Country Link
US (1) US6660890B1 (https=)
EP (1) EP1187798B8 (https=)
JP (1) JP2003503372A (https=)
AT (1) ATE329893T1 (https=)
AU (1) AU1379200A (https=)
DE (1) DE69931966T2 (https=)
WO (1) WO2001000545A1 (https=)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1291336A3 (en) * 2001-09-05 2003-10-08 Solvias AG Preparation of optically active alpha-hydroxyethers
EP1354883A1 (en) * 2002-04-16 2003-10-22 Solvias AG Hydrogenation of prochiral ketones

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8338325B2 (en) * 2002-08-15 2012-12-25 Velocys, Inc. Tethered catalyst processes in microchannel reactors and systems containing a tethered catalyst or tethered chiral auxiliary
JP5346434B2 (ja) * 2006-08-01 2013-11-20 国立大学法人北海道大学 β，β―ビスへテロ置換光学活性アルコールの製造方法
DE102007028924A1 (de) * 2007-06-22 2008-12-24 Saltigo Gmbh Verfahren zur Herstellung von 2-Hydroxyacetalen und den dazu korrespondierenden 2-Hydroxyalkanalen

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5823861B2 (ja) * 1979-06-05 1983-05-18 工業技術院長 α−ケトエステルの不斉水素化方法

Non-Patent Citations (5)

* Cited by examiner, † Cited by third party
Title
B. T. CHO: "Asymmetric reduction of alpha-keto acetals with potassium 9-O-(1,2-isopropylidene-5-deoxy-D-xylofuranosyl)-9-boratabicyclo[3.3.1]nonane. Enantioselective synthesis of alpha-hydroxy acetals with high optical purities", TETRAHEDRON: ASYMMETRY., vol. 5, no. 7, 1994, OXFORD GB, pages 1147 - 1150, XP002131085 *
H. TAKAHASHI: "Highly effective catalytic asymmetric hydrogenations of alpha-keto esters and an alpha-keto acetal with new neutral chiral pyrrolidinebisphosphine-rhodium complexes", CHEMISTRY LETTERS, no. 5, May 1987 (1987-05-01), TOKYO JP, pages 855 - 858, XP002131086 *
H. U. BLASER: "Enantioselective hydrogenation of alpha-ketoesters with cinchona-modified platinum catalysts: effect of acidic and basic solvents and additives", JOURNAL OF MOLECULAR CATALYSIS, vol. 68, 1991, pages 215 - 222, XP000870037 *
M. STRUDER: "Enantioselective hydrogenation of alpha-keto acetals with cinchona modified Pt catalyst", JOURNAL OF THE CHEMICAL SOCIETY, CHEMICAL COMMUNICATIONS, no. 17, 7 September 1999 (1999-09-07), LETCHWORTH GB, pages 1727 - 1728, XP002131088 *
M. STUDER: "Hydrogenation of butane-2,3-dione with heterogeneous cinchona modified platinum catalysts: a combination of an enantioselective reaction and kinetic resolution", JOURNAL OF THE CHEMICAL SOCIETY, CHEMICAL COMMUNICATIONS, no. 9, 7 May 1998 (1998-05-07), LETCHWORTH GB, pages 1053 - 1054, XP002131087 *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1291336A3 (en) * 2001-09-05 2003-10-08 Solvias AG Preparation of optically active alpha-hydroxyethers
EP1354883A1 (en) * 2002-04-16 2003-10-22 Solvias AG Hydrogenation of prochiral ketones

Also Published As

Publication number Publication date
DE69931966D1 (de) 2006-07-27
DE69931966T2 (de) 2007-01-04
EP1187798A1 (en) 2002-03-20
US6660890B1 (en) 2003-12-09
JP2003503372A (ja) 2003-01-28
EP1187798B8 (en) 2006-10-25
AU1379200A (en) 2001-01-31
EP1187798B1 (en) 2006-06-14
ATE329893T1 (de) 2006-07-15

Similar Documents

Publication Publication Date Title
Gladiali et al. Optically active phenanthrolines in asymmetric catalysis. III. Highly efficient enantioselective transfer hydrogenation of acetophenone by chiral rhodium/3-alkyl phenanthroline catalysts.
Berkessel et al. Light-induced enantioselective hydrogenation using chiral derivatives of Casey’s iron–cyclopentadienone catalyst
Willoughby et al. Asymmetric titanocene-catalyzed hydrogenation of imines
Sawamura et al. Enantioselective allylation of nitro group-stabilized carbanions catalyzed by chiral crown ether Phosphine− palladium complexes
Wang et al. Enantioselective hydrogenation of α-ketoamides over Pt/Al2O3 modified by cinchona alkaloids
Fraile et al. Chiral lewis acids supported on silica gel and alumina, and their use as catalysts in Diels-Alder reactions of methacrolein and bromoacrolein
Wang et al. New chiral modifiers for the enantioselective hydrogenation of ethyl pyruvate over Pt/Al2O3 catalysts
US20090326274A1 (en) Sulphonylated Diphenylethylenediamines, Method for Their Preparation and Use in Transfer Hydrogenation Catalysis
Tálas et al. Natural alkaloids and synthetic relatives as chiral templates of the Orito's reaction
US6660890B1 (en) Production of optically active α-hydroxyacetals
Fogassy et al. Enantioselective hydrogenation of exocyclic α, β-unsaturated ketones: Part III. Hydrogenation with Pd in the presence of cinchonidine
US4290961A (en) Process for catalytically reducing carbonyl compounds
CN111004102A (zh) 一种制备光学活性香茅醛的方法及用于该方法的催化剂
Thorey et al. Palladium on Charcoal plus Enantiopure Amino Alcohols as Catalytic Systems for the Enantioselective 1, 4‐Reduction of α‐Substituted α, β‐Unsaturated Ketones
US4925990A (en) Process for the preparation of unsaturated alcohols
US6617475B2 (en) Preparation of optically active α-hydroxyethers
Tungler et al. Asymmetric heterogeneous catalytic hydrogenation, is it a useful tool for the synthetic organic chemist
WO2006002470A1 (en) Chiral ligands for asymmetric catalysis
EP1354883B1 (en) Hydrogenation of prochiral ketones
JPWO2003076072A1 (ja) 実用的キラルジルコニウム触媒
CN115960007B (zh) 一种利用含氮甲酰基催化剂的西格列汀中间体的制备方法
CN110845547A (zh) 一种手性双齿配体、催化剂及其制备方法和应用
Srivastava Preparation of ionic liquid supported organocatalysts for the synthesis of stereoselective (R)-9-Methyl-5 (10)-Octaline-1, 6-Dione
JPH0825910B2 (ja) 光学活性な脂肪族ヒドロキシカルボン酸の製造方法
Gomes Jr et al. Enantioselective heterogeneous catalytic production of alpha-amino acids

Legal Events

Date Code Title Description
ENP Entry into the national phase

Ref country code: AU

Ref document number: 2000 13792

Kind code of ref document: A

Format of ref document f/p: F

AK Designated states

Kind code of ref document: A1

Designated state(s): AE AL AM AT AU AZ BA BB BG BR BY CA CH CN CR CU CZ DE DK EE ES FI GB GD GE GH GM HR HU ID IL IN IS JP KE KG KP KR KZ LC LK LR LS LT LU LV MA MD MG MK MN MW MX NO NZ PL PT RO RU SD SE SG SI SK SL TJ TM TR TT TZ UA UG US UZ VN YU ZA ZW

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): GH GM KE LS MW SD SL SZ TZ UG ZW AM AZ BY KG KZ MD RU TJ TM AT BE CH CY DE DK ES FI FR GB GR IE IT LU MC NL PT SE BF BJ CF CG CI CM GA GN GW ML MR NE SN TD TG

DFPE Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101)
121 Ep: the epo has been informed by wipo that ep was designated in this application
REG Reference to national code

Ref country code: DE

Ref legal event code: 8642

WWE Wipo information: entry into national phase

Ref document number: 1999973927

Country of ref document: EP

ENP Entry into the national phase

Ref country code: JP

Ref document number: 2001 506961

Kind code of ref document: A

Format of ref document f/p: F

WWE Wipo information: entry into national phase

Ref document number: 10018365

Country of ref document: US

WWP Wipo information: published in national office

Ref document number: 1999973927

Country of ref document: EP

WWG Wipo information: grant in national office

Ref document number: 1999973927

Country of ref document: EP