Synlett 2006(13): 2119-2123  
DOI: 10.1055/s-2006-948201
LETTER
© Georg Thieme Verlag Stuttgart · New York

Enantiotopic Desymmetrization of a Cyclic endo-Peroxide by Asymmetric Dialkylzinc Addition

Robert Ernst Ziegert, Stefan Bräse*
Institut für Organische Chemie, Universität Karlsruhe (TH), Fritz-Haber-Weg 6, 76131 Karlsruhe, Germany
Fax: +49(721)6088581; e-Mail: braese@ioc.uka.de;
Weitere Informationen

Publikationsverlauf

Received 12 April 2006
Publikationsdatum:
09. August 2006 (online)

Abstract

The desymmetrization reaction is a common strategy to synthesize complex chiral molecules. The selective cleavage of ­carbon-carbon or carbon-heteroatom bonds is well known, whereas the enantioselective cleavage of heteroatom-heteroatom bonds has been used less extensively. We demonstrate the enantiotopic ­addition of dialkyl zinc reagents to a bicyclic endo-peroxide using chiral [2.2]paracyclophane-based N,O-ligands as a new approach to chiral 4-alkoxy-substituted cyclohexenones.

11

The Supporting Information containing general remarks, synthesis details, analytical details (NMR, IR, MS, HRMS, HPLC) and complete tabelaric results are available from the authors.