EP 1899313 A1 20080319 - METHOD FOR PRODUCING SINGLE ENANTIOMER EPOXIDES BY THE ADH REDUCTION OF ALPHA-LEAVING GROUP-SUBSTITUTED KETONES AND CYCLISATION
Title (en)
METHOD FOR PRODUCING SINGLE ENANTIOMER EPOXIDES BY THE ADH REDUCTION OF ALPHA-LEAVING GROUP-SUBSTITUTED KETONES AND CYCLISATION
Title (de)
VERFAHREN ZUR HERSTELLUNG VON ENANTIOMERENREINEN EPOXIDEN DURCH ADH-REDUKTION VON ALPHA-ABGANGSGRUPPEN-SUBSTITUIERTEN KETONEN UND CYCLISIERUNG
Title (fr)
PROCEDE DE PRODUCTION D'EPOXYDES EXEMPTS D'ENANTIOMERES PAR REDUCTION ADH DE CETONES A SUBSTITUTION D'ALPHA-NUCLEOFUGES ET CYCLISATION
Publication
Application
Priority
- EP 2006005437 W 20060607
- DE 102005028312 A 20050618
Abstract (en)
[origin: DE102005028312A1] Preparation of enantiomerically pure epoxides (A) comprises reducing alpha -leaving group-substituted ketones (I) with (R)- or (S)-selective alcohol dehydrogenases (ADH) in the presence of a cofactor and optionally a system for regenerating the oxidized cofactor to give corresponding enantiomerically pure alcohols (B) and subsequent cyclization using a base. Preparation of enantiomerically pure epoxides (A) of formula (IIIa) or (IIIb) comprises reducing alpha -leaving group-substituted ketone compounds (I) of formula (R 1-CO-C(R 2)(R 3)(LG)) with (R)- or (S)-selective alcohol dehydrogenase (ADH) in the presence of a cofactor and optionally a system for regenerating the oxidized cofactor to give corresponding enantiomerically pure alcohols (B) of formula (IIa) or (IIb) and subsequent cyclization using a base. LG : F, Cl, Br, I, OSO 2Ar, OSO 2CH 3, OSO 2R or OP(O)OR 2; and R 1-R 3H, optionally substituted 1-20C alkyl, optionally substituted 3-10C cycloalkyl, alkenyl, optionally substituted (hetero)aryl, CO 2R, CONR 2, COSR, CS 2R, C(NH)NR 2, CN, CHal 3, ArO, ArS, RO, RS, CHO, OH, NHR, NR 2, Cl, F, Br, I or SiR 3. [Image].
IPC 8 full level
C07D 303/08 (2006.01)
CPC (source: EP US)
C07D 301/26 (2013.01 - EP US); C07D 303/08 (2013.01 - EP US)
Designated contracting state (EPC)
AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IS IT LI LT LU LV MC NL PL PT RO SE SI SK TR
DOCDB simple family (publication)
DE 102005028312 A1 20061228; DE 102005028312 B4 20080508; CA 2612407 A1 20061228; CN 101184742 A 20080521; EP 1899313 A1 20080319; JP 2008543293 A 20081204; US 2008206826 A1 20080828; WO 2006136289 A1 20061228
DOCDB simple family (application)
DE 102005028312 A 20050618; CA 2612407 A 20060607; CN 200680018341 A 20060607; EP 06754193 A 20060607; EP 2006005437 W 20060607; JP 2008516180 A 20060607; US 91777706 A 20060607