Synthesis 2009(2): 335-338  
DOI: 10.1055/s-0028-1083275
PSP
© Georg Thieme Verlag Stuttgart ˙ New York

Enantioselective Rhodium-Catalyzed Alkylative Desymmetrization of 3,5-Dimethylglutaric Anhydride

Matthew J. Cook, Tomislav Rovis*
Department of Chemistry, Colorado State University, Fort Collins, CO 80523, USA
Fax: +1(970)4911801; e-Mail: rovis@lamar.colostate.edu;
Further Information

Publication History

Received 16 June 2008
Publication Date:
12 December 2008 (eFirst)

Abstract

A rhodium-catalyzed enantioselective cross-coupling of sp³ organozinc reagents and 3,5-dimethylglutaric anhydride has been developed to afford the corresponding products, syn-deoxypolypropionates, in excellent yields and enantioselectivities. This reaction has been developed so that both commercially available and in situ prepared organozinc reagents are competent coupling partners.

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9

The reaction proceeds in a cleaner fashion if the Grignard is prepared in situ, to avoid by-products arising from oxidation of the organometallic.