Catalytic Asymmetric Synthesis of Chiral Allylic Esters

Jeffrey S. Cannon, Stefan F. Kirsch and Larry E. Overman*

*Department of Chemistry, 1102 Natural Sciences II, University of California, Irvine, California 92697-2025, Email: leovermauci.edu

J. S. Cannon, S. F. Kirsch, L. E. Overman, J. Am. Chem. Soc., 2010, 132, 15185-15191.

DOI: 10.1021/ja106685w

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Abstract

Trichloroacetimidates of allylic alcohols, either generated in situ or in a separate step, undergo clean enantioselective S_N2′ substitution with various carboxylic acids in the presence of a chiral palladium(II) catalyst. The scope and limitations of this useful catalytic asymmetric allylic esterification are defined.

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Key Words

Allylic Alcohols

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ID: J48-Y2010-3020