Premium
New Routes to Chiral Evans Auxiliaries by Enzymatic Desymmetrisation and Resolution Strategies
Author(s) -
Neri Claudia,
Williams Jonathan M. J.
Publication year - 2003
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/adsc.200303006
Subject(s) - chemistry , lipase , enantiomer , yield (engineering) , pancreatic lipase , enantioselective synthesis , organic chemistry , resolution (logic) , enzyme , stereochemistry , kinetic resolution , triacylglycerol lipase , catalysis , materials science , artificial intelligence , computer science , metallurgy
This paper describes how enantiomerically enriched Evans auxiliaries can be successfully prepared by either an enzymatic desymmetrisation strategy or an asymmetric synthesis using racemic auxiliaries and an enzymatic resolution. Desymmetrisation of N ‐Boc‐protected serinol has been achieved in good yield and high enantiomeric excess using porcine pancreas lipase. This has been exploited in different ways to prepare enantiomerically enriched (4 R )‐ and (4 S )‐substituted 2‐oxazolidinones. In another approach to asymmetric synthesis, starting from a racemic Evans auxiliary, by means of a diastereoselective aldol reaction coupled with a lipase‐catalysed resolution, we achieved the preparation of enantiomerically enriched β‐hydroxy acids and enantiomerically enriched 2‐oxazolidinones.