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Synfacts 2006(12): 1239-1239  
DOI: 10.1055/s-2006-949497
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Catalytic Enantioselective Decarboxylation-Protonation

Contributor(s): Hisashi Yamamoto, Matthew B. Boxer
J. T. Mohr, T. Nishimata, D. C. Behenna, B. M. Stoltz*
California Institute of Technology, Pasadena, USA
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Publication History

Publication Date:
22 November 2006 (online)

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Significance

Asymmetric protonation remains an important challenge in organic chemistry. This report by Stoltz does an excellent job of extending their previous allylation work to protonation using formic acid as the achiral proton source. A variety of substrates are tolerated giving moderate to high enantioselectivity (60-95% ee). While only cyclic ketones are described, both fused aromatic and alkyl carbocycles work, as well as heterocyclic compounds.