WO2008064817A3 - Method for the stereoselective synthesis of chiral epoxides by adh reduction of ketones substituted with alpha starting groups and cyclisation - Google Patents

Method for the stereoselective synthesis of chiral epoxides by adh reduction of ketones substituted with alpha starting groups and cyclisation Download PDF

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Publication number
WO2008064817A3
WO2008064817A3 PCT/EP2007/010125 EP2007010125W WO2008064817A3 WO 2008064817 A3 WO2008064817 A3 WO 2008064817A3 EP 2007010125 W EP2007010125 W EP 2007010125W WO 2008064817 A3 WO2008064817 A3 WO 2008064817A3
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WO
WIPO (PCT)
Prior art keywords
optionally substituted
radical
chiral
substituted
cyclisation
Prior art date
Application number
PCT/EP2007/010125
Other languages
German (de)
French (fr)
Other versions
WO2008064817A2 (en
Inventor
Andreas Meudt
Richard A Wisdom
Original Assignee
Archimica Gmbh
Andreas Meudt
Richard A Wisdom
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 Archimica Gmbh, Andreas Meudt, Richard A Wisdom filed Critical Archimica Gmbh
Priority to EP07846734A priority Critical patent/EP2086952A2/en
Publication of WO2008064817A2 publication Critical patent/WO2008064817A2/en
Publication of WO2008064817A3 publication Critical patent/WO2008064817A3/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/08—Compounds containing oxirane rings with hydrocarbon radicals, substituted by halogen atoms, nitro radicals or nitroso radicals

Abstract

The invention relates to a method for producing chiral epoxides by reducing ketones substituted with α-starting groups with cell-free (R)- or (S)-selective alcohol dehydrogenases in the presence of a cofactor, and optionally a suitable system for the regeneration of the oxidised cofactor to form the chiral alcohols, and subsequent base-induced cyclisation to form the chiral epoxides (EQUATION 1) wherein LG can represent F, Cl, Br, I, OSO2Ar, OSO2R4 or OP(O)OR4R5 and R1, R2 and R3 independently represent hydrogen, a branched or unbranched, optionally substituted C1-C20 alkyl radical, an optionally substituted C3-C10 cycloalkyl or alkenyl radical or an optionally substituted carbocyclic or heterocyclic aryl radical or a radical from the group consisting of CO2R4, CONR4R5, COSR4, CS2R4, C(NH)NR4R5, CN, CHaI3, OAr, SAr, OR4, SR4, CHO, OH, NR4R5, Cl, F, Br, I or SiR4R5R6, where R4, R5 and R6 independently represent hydrogen, a branched or unbranched, optionally substituted C1-C20 alkyl radical, an optionally substituted C3-C10 cycloalkyl or alkenyl radical or a substituted carbocylic or heterocyclic aryl radical, the intermediately formed chiral alcohol Il not being isolated.
PCT/EP2007/010125 2006-11-30 2007-11-22 Method for the stereoselective synthesis of chiral epoxides by adh reduction of ketones substituted with alpha starting groups and cyclisation WO2008064817A2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP07846734A EP2086952A2 (en) 2006-11-30 2007-11-22 Method for the stereoselective synthesis of chiral epoxides by adh reduction of ketones substituted with alpha starting groups and cyclisation

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE200610056526 DE102006056526A1 (en) 2006-11-30 2006-11-30 Process for the stereoselective synthesis of chiral epoxides by ADH reduction of alpha-leaving group-substituted ketones and cyclization
DE102006056526.6 2006-11-30

Publications (2)

Publication Number Publication Date
WO2008064817A2 WO2008064817A2 (en) 2008-06-05
WO2008064817A3 true WO2008064817A3 (en) 2008-07-17

Family

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Family Applications (1)

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PCT/EP2007/010125 WO2008064817A2 (en) 2006-11-30 2007-11-22 Method for the stereoselective synthesis of chiral epoxides by adh reduction of ketones substituted with alpha starting groups and cyclisation

Country Status (3)

Country Link
EP (1) EP2086952A2 (en)
DE (1) DE102006056526A1 (en)
WO (1) WO2008064817A2 (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9410166B2 (en) 2009-12-29 2016-08-09 Butamax Advanced Biofuels Llc Alcohol dehydrogenases (ADH) useful for fermentive production of lower alkyl alcohols

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WO2009024823A2 (en) 2007-08-22 2009-02-26 Astrazeneca Ab Oxadiazole derivatives as dgat inhibitors
TW201039825A (en) 2009-02-20 2010-11-16 Astrazeneca Ab Cyclopropyl amide derivatives 983
CA2765566C (en) 2009-06-22 2016-04-12 Sk Biopharmaceuticals Co., Ltd. Method for preparation of carbamic acid (r)-1-aryl-2-tetrazolyl-ethyl ester
US8404461B2 (en) 2009-10-15 2013-03-26 SK Biopharmaceutical Co. Ltd. Method for preparation of carbamic acid (R)-1-aryl-2-tetrazolyl-ethyl ester
EP2536702A4 (en) 2010-02-18 2013-07-10 Astrazeneca Ab New crystalline form of a cyclopropyl benzamide derivative
EP2643467A1 (en) * 2010-11-24 2013-10-02 Basf Se Method for producing n-heterocyclic optically active alcohols
US20130273619A1 (en) 2012-04-16 2013-10-17 Basf Se Process for the Preparation of (3E, 7E)-Homofarnesol
CN113831218B (en) * 2020-06-23 2023-11-28 利尔化学股份有限公司 Method for preparing 4-fluorophenyl ethylene oxide

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0493617A1 (en) * 1990-07-24 1992-07-08 Kanegafuchi Kagaku Kogyo Kabushiki Kaisha Process for producing optically active (-)-2-halo-1-(substituted phenyl)ethanol and (-)-substituted styrene oxide
WO2002064579A1 (en) * 2001-02-09 2002-08-22 Forschungszentrum Jülich GmbH Method for producing optically active, propargylic terminal epoxides
EP1568780A1 (en) * 2004-02-12 2005-08-31 Consortium für elektrochemische Industrie GmbH Enzymatic method for the enantioselective reduction of keto compounds
WO2006136289A1 (en) * 2005-06-18 2006-12-28 Archimica Gmbh Method for producing single enantiomer epoxides by the adh reduction of alpha-leaving group-substituted ketones and cyclisation

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0493617A1 (en) * 1990-07-24 1992-07-08 Kanegafuchi Kagaku Kogyo Kabushiki Kaisha Process for producing optically active (-)-2-halo-1-(substituted phenyl)ethanol and (-)-substituted styrene oxide
WO2002064579A1 (en) * 2001-02-09 2002-08-22 Forschungszentrum Jülich GmbH Method for producing optically active, propargylic terminal epoxides
EP1568780A1 (en) * 2004-02-12 2005-08-31 Consortium für elektrochemische Industrie GmbH Enzymatic method for the enantioselective reduction of keto compounds
WO2006136289A1 (en) * 2005-06-18 2006-12-28 Archimica Gmbh Method for producing single enantiomer epoxides by the adh reduction of alpha-leaving group-substituted ketones and cyclisation

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9410166B2 (en) 2009-12-29 2016-08-09 Butamax Advanced Biofuels Llc Alcohol dehydrogenases (ADH) useful for fermentive production of lower alkyl alcohols

Also Published As

Publication number Publication date
EP2086952A2 (en) 2009-08-12
DE102006056526A1 (en) 2008-06-05
WO2008064817A2 (en) 2008-06-05

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