Catalytic Enantioselective Decarboxylative Protonation

Justin T. Mohr, Toyoki Nishimata, Douglas C. Behenna, and Brian M. Stoltz*
Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125
J. Am. Chem. Soc., 2006, 128 (35), pp 11348–11349
DOI: 10.1021/ja063335a
Publication Date (Web): August 15, 2006
Copyright © 2006 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, stoltz@caltech.edu

Abstract

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We report a highly enantioselective, general catalytic system for the facile synthesis of tertiary stereocenters by protonation adjacent to cyclic ketones. The method relies on catalytic decarboxylative protonation of readily accessible racemic quaternary β-ketoesters. A range of substituted cycloalkanone compounds can be accessed through this process with high levels of enantioselectivity.

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History

  • Published In Issue September 06, 2006
  • Received May 17, 2006

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