AU659929B2 - Enantioselective oxazaborolidine catalysts - Google Patents

Enantioselective oxazaborolidine catalysts Download PDF

Info

Publication number
AU659929B2
AU659929B2 AU35931/93A AU3593193A AU659929B2 AU 659929 B2 AU659929 B2 AU 659929B2 AU 35931/93 A AU35931/93 A AU 35931/93A AU 3593193 A AU3593193 A AU 3593193A AU 659929 B2 AU659929 B2 AU 659929B2
Authority
AU
Australia
Prior art keywords
phenyl
international
carbon atom
chiral
document
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
AU35931/93A
Other languages
English (en)
Other versions
AU3593193A (en
Inventor
George J Quallich
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.)
Pfizer Inc
Original Assignee
PFIZER
Pfizer Inc
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 PFIZER, Pfizer Inc filed Critical PFIZER
Publication of AU3593193A publication Critical patent/AU3593193A/en
Application granted granted Critical
Publication of AU659929B2 publication Critical patent/AU659929B2/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
    • C07D213/30—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
    • C07F5/02—Boron compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
    • C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
    • C07C29/143—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of ketones
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D277/24—Radicals substituted by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
    • C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
    • C07F5/02—Boron compounds
    • C07F5/025—Boronic and borinic acid compounds
    • 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
    • C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
    • C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
    • C07C2601/10—Systems containing only non-condensed rings with a five-membered ring the ring being unsaturated

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)
  • Physical Or Chemical Processes And Apparatus (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Catalysts (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pyridine Compounds (AREA)
  • Polyurethanes Or Polyureas (AREA)
AU35931/93A 1992-05-14 1993-02-01 Enantioselective oxazaborolidine catalysts Ceased AU659929B2 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US88331792A 1992-05-14 1992-05-14
US883317 1992-05-14
PCT/US1993/000687 WO1993023408A1 (en) 1992-05-14 1993-02-01 Enantioselective oxazaborolidine catalysts

Publications (2)

Publication Number Publication Date
AU3593193A AU3593193A (en) 1993-12-13
AU659929B2 true AU659929B2 (en) 1995-06-01

Family

ID=25382382

Family Applications (1)

Application Number Title Priority Date Filing Date
AU35931/93A Ceased AU659929B2 (en) 1992-05-14 1993-02-01 Enantioselective oxazaborolidine catalysts

Country Status (21)

Country Link
US (1) US5552548A (cg-RX-API-DMAC7.html)
EP (1) EP0640089B1 (cg-RX-API-DMAC7.html)
JP (1) JP2525127B2 (cg-RX-API-DMAC7.html)
KR (2) KR950701637A (cg-RX-API-DMAC7.html)
AT (1) ATE146790T1 (cg-RX-API-DMAC7.html)
AU (1) AU659929B2 (cg-RX-API-DMAC7.html)
CA (1) CA2134096C (cg-RX-API-DMAC7.html)
DE (1) DE69306945T2 (cg-RX-API-DMAC7.html)
DK (1) DK0640089T3 (cg-RX-API-DMAC7.html)
ES (1) ES2096275T3 (cg-RX-API-DMAC7.html)
FI (1) FI107259B (cg-RX-API-DMAC7.html)
GR (1) GR3022171T3 (cg-RX-API-DMAC7.html)
HU (1) HU215089B (cg-RX-API-DMAC7.html)
IL (1) IL105623A (cg-RX-API-DMAC7.html)
MX (1) MX9302785A (cg-RX-API-DMAC7.html)
MY (1) MY111251A (cg-RX-API-DMAC7.html)
NO (1) NO300500B1 (cg-RX-API-DMAC7.html)
NZ (1) NZ249302A (cg-RX-API-DMAC7.html)
TW (1) TW232696B (cg-RX-API-DMAC7.html)
WO (1) WO1993023408A1 (cg-RX-API-DMAC7.html)
ZA (1) ZA933340B (cg-RX-API-DMAC7.html)

Families Citing this family (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH06329679A (ja) * 1993-01-20 1994-11-29 Nissan Chem Ind Ltd 光学活性β−アミノアルコキシボラン錯体
TW416958B (en) * 1993-05-14 2001-01-01 Pfizer Enantioselective oxazaborolidine catalysts
CA2167287A1 (en) * 1993-07-16 1995-01-26 George Joseph Quallich Enantioselective process for thiazole intermediates
EP0724552B1 (en) * 1993-11-30 1997-10-29 Pfizer Inc. Process for preparing a chiral tetralone
US5495054A (en) * 1994-05-31 1996-02-27 Sepracor, Inc. Tetrahydroindeno[1,2-D][1,3,2]oxazaboroles and their use as enantioselective catalysts
AU2792497A (en) * 1996-09-18 1998-04-14 Shionogi & Co., Ltd. Process for preparing optically acitve alcohol by reduction with asymmetric borane
ES2130083B1 (es) * 1997-08-04 2000-01-16 Esteve Labor Dr Procedimiento para la obtencion de los enantiomeros de cizolirtina.
US6509472B2 (en) * 2000-09-11 2003-01-21 Schering Corporation 4-Cyclohexyl-1,3,2-oxazaborolidine chiral accessories
DK2035437T3 (da) * 2006-06-26 2010-11-29 Basf Se Boran-æter-komplekser
US20080242877A1 (en) * 2007-02-26 2008-10-02 Vinod Kumar Kansal Intermediates and processes for the synthesis of Ramelteon
US7838691B2 (en) * 2007-04-05 2010-11-23 Board Of Regents, Of The University Of Texas System Palmerolides: methods of preparation and derivatives thereof
JP2010526075A (ja) * 2007-04-30 2010-07-29 アドロー コーポレイション （−）−ｅ−１０−ｏｈ−ｎｔの組成物、ならびにそれらの合成および使用のための方法
US8084630B2 (en) * 2007-05-31 2011-12-27 Teva Pharmaceutical Industries Ltd. Process for the synthesis of ramelteon and its intermediates
US20090082568A1 (en) * 2007-09-21 2009-03-26 Basf Aktiengesellschaft Accelerated reduction of organic substances with boranes
US20090281176A1 (en) * 2007-11-01 2009-11-12 Vinod Kumar Kansal Process for the synthesis of ramelteon and its intermediates
US20100152468A1 (en) * 2008-10-16 2010-06-17 Teva Pharmaceutical Industries Ltd. Process for the synthesis of ramelteon and its intermediates

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU5843194A (en) * 1993-01-20 1994-08-15 Nissan Chemical Industries Ltd. Optically active beta -aminoalkoxyborane complex
AU6289694A (en) * 1993-05-14 1994-12-12 Pfizer Inc. Enantioselective oxazaborolidine catalysts

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4943635A (en) * 1987-08-27 1990-07-24 President & Fellows Of Harvard College Enantioselective reduction of ketones
US5157129A (en) * 1990-04-18 1992-10-20 Merck & Co., Inc. Enantiospecific synthesis of s-(+)-5,6-dihydro-4-(r-amino)-4h-thieno(2,3-b)thiopyran-2-sulfonamide-7,7-dioxide
US5039802A (en) * 1990-04-18 1991-08-13 Merck & Co., Inc. Arylation process for preparation of chiral catalysts for ketone reduction

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU5843194A (en) * 1993-01-20 1994-08-15 Nissan Chemical Industries Ltd. Optically active beta -aminoalkoxyborane complex
AU6289694A (en) * 1993-05-14 1994-12-12 Pfizer Inc. Enantioselective oxazaborolidine catalysts

Also Published As

Publication number Publication date
EP0640089A1 (en) 1995-03-01
KR0149208B1 (ko) 1998-10-15
FI932174L (fi) 1993-11-15
KR950701637A (ko) 1995-04-28
ZA933340B (en) 1994-11-14
MX9302785A (es) 1994-02-28
JPH07503734A (ja) 1995-04-20
GR3022171T3 (en) 1997-03-31
US5552548A (en) 1996-09-03
JP2525127B2 (ja) 1996-08-14
AU3593193A (en) 1993-12-13
FI107259B (fi) 2001-06-29
EP0640089B1 (en) 1996-12-27
HUT65136A (en) 1994-04-28
DK0640089T3 (da) 1997-06-16
ES2096275T3 (es) 1997-03-01
FI932174A0 (fi) 1993-05-13
TW232696B (cg-RX-API-DMAC7.html) 1994-10-21
MY111251A (en) 1999-10-30
NZ249302A (en) 1996-11-26
HU215089B (hu) 1998-09-28
DE69306945D1 (de) 1997-02-06
CA2134096A1 (en) 1993-11-25
ATE146790T1 (de) 1997-01-15
NO944297D0 (no) 1994-11-11
IL105623A (en) 1998-02-22
CA2134096C (en) 1997-11-25
WO1993023408A1 (en) 1993-11-25
DE69306945T2 (de) 1997-05-07
IL105623A0 (en) 1993-09-22
HU9301395D0 (en) 1993-09-28
NO300500B1 (no) 1997-06-09
NO944297L (no) 1994-11-11

Similar Documents

Publication Publication Date Title
Puigjaner et al. A new family of modular chiral ligands for the catalytic enantioselective reduction of prochiral ketones
US5552548A (en) Enantioselective oxazaborolidine catalysts
AU674067B2 (en) Enantioselective oxazaborolidine catalysts
Gommermann et al. Practical highly enantioselective synthesis of terminal propargylamines. An expeditious synthesis of (S)-(+)-coniine
Asami et al. Enantioselective addition of dialkylzinc to aldehydes catalyzed by (S)-2-(N, N-disubstituted aminomethyl) indoline
Suri et al. Enantioselective reduction of aryl ketones using LiBH4 and TarB-X: a chiral Lewis acid
Deur et al. Photochemical reaction between tertiary allylic amines and chromium carbene complexes: Synthesis of lactams via a zwitterion aza cope rearrangement
Widhalm et al. Chiral ferrocene derivatives containing a 2, 2′-bridged binaphthyl moiety
AU689595B2 (en) Tetrahydroindeno(1,2-d)(1,3,2)oxazaboroles and their use as enantioselective catalysts
EP1458729B1 (fr) Composes (aryl) (amino)boranes, procede pour leur preparation
Goralski et al. Boranes in synthesis—VII. Synthesis of 2-dialkylamino-6, 6-dimethylbicyclo [3.1. 1] heptan-3-ols from (R)-(+)-nopinone. Chiral auxiliaries for the addition of diethylzinc to aromatic aldehydes
Kurosu et al. Highly diastereofacial anti-aldol reaction: practical synthesis of optically active anti-2-alkyl-3-hydroxycarboxylic acid ester units
Munoz-Hernandez et al. Highly Functionalized tertiary-Carbinols and Carbinamines from the Asymmetric γ‑Alkoxyallylboration of Ketones and Ketimines with the Borabicyclodecanes
Dhokte et al. Chiral synthesis via organoboranes. 48. Efficient synthesis of trans-fused bicyclic and cyclic ketones and secondary alcohols in high optical purities via asymmetric cyclic hydroboration with isopinocampheylchloroborane etherate
Gibson et al. Application of chiral lithium amide base chemistry to the synthesis of planar chiral (arene) tricarbonylchromium (0) complexes
JP3976357B2 (ja) 光学活性アルコールの製造方法
EP0901996B1 (en) Process for producing optically active amines
Chindan et al. Ligand Controlled Regiodivergent Synthesis of α-Tertiary and Quaternary Alkyl-Alkoxysilanes
Kawashima et al. Formation of a 1, 3, 2, 4-Dioxadiborinanide, a Novel Boron-Containing Heterocycle, by Hydrolysis of a Tetracoordinate 1, 2-Oxaboretanide and Its Crystal Structure
Coeffard et al. Synthesis of Highly Enantioenriched Chiral α-Aminoorganotins via Diastereoselective Ring Opening of Chiral N-(Arenesulfonyl) 2-Tributylstannyloxazolidines
JPWO2011062280A1 (ja) 光学活性アルコールの製造方法
Castaldi et al. Synthesis of An Enantioenriched C2‐Symmetric Molecule by a Chiral‐Base‐Mediated Kinetic Resolution of an (Arene) tricarbonylchromium (0) Complex
EP0708764A1 (en) Enanthioselective preparation of thiazole derivatives

Legal Events

Date Code Title Description
MK14 Patent ceased section 143(a) (annual fees not paid) or expired