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DOI: 10.1055/s-2007-969019
Rhodium-Catalyzed Enantioselective Desymmetrization
M. J. Cook, T. Rovis*
Colorado State University, Fort Collins, USA
Publication History
Publication Date:
07 November 2007 (online)
![](https://www.thieme-connect.de/media/synfacts/200710/lookinside/thumbnails/10.1055-s-2007-969019-1.jpg)
Significance
A rhodium-catalyzed enantioselective desymmetrization of various glutaric anhydrides with carbon nucleophiles generates syn-deoxypolypropionate synthons in good yields and high ee values. The nucleophiles are commercially available or in situ generated alkyl or benzyl zinc reagents; aryl nucleophiles, however, are not compatible. A good range of alkyl nucleophiles, including those with an ester or chloride moiety, is shown. Electron-rich benzylic nucleophiles result in lower ee values due to a background reaction. Some examples of post-modifications of the product are also provided, including a deoxygenation and a diastereoselective reduction producing an intermediate to the synthesis of a beetle pheromone.