EP 2086952 A2 20090812 - METHOD FOR THE STEREOSELECTIVE SYNTHESIS OF CHIRAL EPOXIDES BY ADH REDUCTION OF KETONES SUBSTITUTED WITH ALPHA STARTING GROUPS AND CYCLISATION
Title (en)
METHOD FOR THE STEREOSELECTIVE SYNTHESIS OF CHIRAL EPOXIDES BY ADH REDUCTION OF KETONES SUBSTITUTED WITH ALPHA STARTING GROUPS AND CYCLISATION
Title (de)
VERFAHREN ZUR STEREOSELEKTIVEN SYNTHESE VON CHIRALEN EPOXIDEN DURCH ADH-REDUKTION VON ALPHA-ABGANGSGRUPPEN-SUBSTITUIERTEN KETONEN UND CYCLISIERUNG
Title (fr)
PROCÉDÉ DE SYNTHÈSE STÉRÉOSÉLECTIVE D'ÉPOXYDES CHIRAUX PAR RÉDUCTION ADH DE CÉTONES SUBSTITUÉES AVEC DES GROUPES PARTANTS ALPHA, ET CYCLISATION
Publication
Application
Priority
- EP 2007010125 W 20071122
- DE 102006056526 A 20061130
Abstract (en)
[origin: WO2008064817A2] The invention relates to a method for producing chiral epoxides by reducing ketones substituted with a-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, OSO<SUB>2</SUB>Ar, OSO<SUB>2</SUB>R<SUB>4</SUB> or OP(O)OR<SUB>4</SUB>R<SUB>5</SUB> and R<SUB>1</SUB>, R<SUB>2</SUB> and R<SUB>3</SUB> independently represent hydrogen, a branched or unbranched, optionally substituted C<SUB>1</SUB>-C<SUB>20</SUB> alkyl radical, an optionally substituted C<SUB>3</SUB>-C<SUB>10 </SUB>cycloalkyl or alkenyl radical or an optionally substituted carbocyclic or heterocyclic aryl radical or a radical from the group consisting of CO<SUB>2</SUB>R<SUB>4</SUB>, CONR<SUB>4</SUB>R<SUB>5</SUB>, COSR<SUB>4</SUB>, CS<SUB>2</SUB>R<SUB>4</SUB>, C(NH)NR<SUB>4</SUB>R<SUB>5</SUB>, CN, CHaI<SUB>3</SUB>, OAr, SAr, OR<SUB>4</SUB>, SR<SUB>4</SUB>, CHO, OH, NR<SUB>4</SUB>R<SUB>5</SUB>, Cl, F, Br, I or SiR<SUB>4</SUB>R<SUB>5</SUB>R<SUB>6</SUB>, where<SUB/>R<SUB>4</SUB>, R<SUB>5</SUB> and R<SUB>6</SUB> independently represent hydrogen, a branched or unbranched, optionally substituted C<SUB>1</SUB>-C<SUB>20</SUB> alkyl radical, an optionally substituted C<SUB>3</SUB>-C<SUB>10 </SUB>cycloalkyl or alkenyl radical or a substituted carbocylic or heterocyclic aryl radical, the intermediately formed chiral alcohol Il not being isolated.
IPC 8 full level
C07D 303/08 (2006.01)
CPC (source: EP)
C07D 303/08 (2013.01)
Citation (search report)
See references of WO 2008064817A2
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 MT NL PL PT RO SE SI SK TR
DOCDB simple family (publication)
DE 102006056526 A1 20080605; EP 2086952 A2 20090812; WO 2008064817 A2 20080605; WO 2008064817 A3 20080717
DOCDB simple family (application)
DE 102006056526 A 20061130; EP 07846734 A 20071122; EP 2007010125 W 20071122