Chiral Epoxides by Desymmetrizing Deprotonation ofmeso-Epoxides

Abstract

Simple meso-epoxides can be asymmetrically functionalized: Ligand-assisted direct hydrogen–lithium exchange allows the generation of destabilized oxiranyl lithium species and their subsequent trapping by a wide array of electrophiles (see scheme; E=group formed by addition of electrophile). When carried out in the presence of (−)-sparteine as ligand, this reaction provides a new enantioselective route to epoxides. Supporting information for this article is available on the WWW under http://www.wiley-vch.de/contents/jc_2002/2002/z18822_s.pdf or from the author. Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.