Research

New routes to chiral Evans auxiliaries by enzymatic desymmetrisation and resolution strategies


Reference:

Neri, C. and Williams, J. M. J., 2003. New routes to chiral Evans auxiliaries by enzymatic desymmetrisation and resolution strategies. Advanced Synthesis & Catalysis, 345 (6-7), pp. 835-848.

Related documents:

This repository does not currently have the full-text of this item.
You may be able to access a copy if URLs are provided below.

Abstract

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 (4R)- and (4S)-substituted 2-oxazolidinones. In an-other 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 beta-hydroxy acids and enantiomerically enriched 2-oxazolidinones.

Details

Item Type Articles
CreatorsNeri, C.and Williams, J. M. J.
DOI10.1002/adsc.200303006
DepartmentsFaculty of Science > Chemistry
RefereedYes
StatusPublished
ID Code4976
Additional InformationID number: ISI:000183660400029

Export

Actions (login required)

View Item