Synthesis 2007(4): 638-641  
DOI: 10.1055/s-2007-965887
PSP
© Georg Thieme Verlag Stuttgart · New York

A Practical Synthesis of Optically Active α-Substituted Ketones in High Enantiomeric­ Excess

Darunee Soorukram, Paul Knochel*
Ludwig-Maximilians-Universität München, Department Chemie und Biochemie, Butenandtstraße 5-13, Haus F, 81377 München, Germany
Fax: +49(89)218077680; e-Mail: paul.knochel@cup.uni-muenchen.de;
Further Information

Publication History

Received 19 October 2006
Publication Date:
12 January 2007 (online)

Abstract

A highly enantioselective synthesis of optically active α-substituted ketones can be achieved by using a reaction sequence involving­ a stereoselective anti-SN2′-allylic substitution in the presence of CuCN·2LiCl, followed by the oxidation of the intermediate cycloalkenyllithium­ species using B(MeO)3/NaBO3·4H2O. The substitution reaction proceeds with a perfect transfer of chirality.