The Enantioselective Organocatalytic 1,4-Addition of Electron-Rich Benzenes to α,β-Unsaturated Aldehydes

Nick A. Paras and David W. C. MacMillan*

*Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, Email: dmacmillcaltech.edu

N. A. Paras, D. W. C. MacMillan, J. Am. Chem. Soc., 2002, 124, 7894-7895.

DOI: 10.1021/ja025981p

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Abstract

The first enantioselective organocatalytic alkylation of electron-rich benzene rings with α,β-unsaturated aldehydes using iminium catalysis has provided a new strategy for the enantioselective construction of benzylic stereogenicity. The (2S,5S)-5-benzyl-2-tert-butylimidazolidinone amine catalyst has been found to mediate the conjugate addition of a wide variety of substituted and unsubstituted anilines to a diverse spectrum of unsaturated aldehydes.

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Key Words

Organocatalysis, Conjugate Addition

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ID: J48-Y2002-1180