Premium
Efficient Lipase‐Catalyzed Kinetic Resolution and Dynamic Kinetic Resolution of β‐Hydroxy Nitriles. A Route to Useful Precursors for γ‐Amino Alcohols
Author(s) -
Pàmies Oscar,
Bäckvall JanE.
Publication year - 2001
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/1615-4169(200108)343:6/7<726::aid-adsc726>3.0.co;2-e
Subject(s) - kinetic resolution , chemistry , racemization , lipase , candida antarctica , transesterification , catalysis , organic chemistry , alkyl , aryl , ruthenium , alcohol , enantioselective synthesis , enzyme
Abstract An efficient kinetic resolution of racemic β‐hydroxy nitriles 1 was performed via Candida antarctica lipase (N‐435)‐catalyzed transesterification . A variety of racemic alkyl, aryl, and aryloxymethyl substituted β‐hydroxy nitriles was efficiently transformed to the corresponding enantiomerically pure acetates (ee > 99% and conversion = 50%) with E values from 40 to >1000. The combination of the enzymatic kinetic resolution with a ruthenium‐catalyzed alcohol racemization led to a dynamic kinetic resolution (ee's up to 99%, yields up to 85%).