Synlett 2007(3): 0485-0487  
DOI: 10.1055/s-2007-967937
LETTER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Enantiomerically Pure Cyclopentene Building Blocks

Lutz F. Tietze*, Christian Stadler, Niels Böhnke, Gordon Brasche, Alexander Grube
Institute for Organic and Biomolecular Chemistry of the Georg-August-University Göttingen, Tammannstraße 2, 37077 Göttingen, Germany
Fax: +49(551)399476; e-Mail: ltietze@gwdg.de;
Further Information

Publication History

Received 23 November 2006
Publication Date:
07 February 2007 (online)

Abstract

An efficient synthesis of the enantiomerically pure cis-annulated cyclopentenes 2 and ent-2 was established by the use of an enzymatic transesterification and hydrolysis, respectively, followed by an SN2-type substitution with a benzyloxymethyl cuprate and a sigmatropic rearrangement. The advantage of this approach is the short sequence combined with an excellent overall yield and an enantiomeric excess of 99%.