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

Abstract

A rhodium-catalyzed enantioselective cross-coupling of sp^³ 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.

Key words

organozinc reagents - Grignard reagents - C-C bond formation - syn-deoxypolypropionates

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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.