The First Direct and Enantioselective Cross-Aldol Reaction of Aldehydes

Alan B. Northrup and David W. C. MacMillan*
Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125
J. Am. Chem. Soc., 2002, 124 (24), pp 6798–6799
DOI: 10.1021/ja0262378
Publication Date (Web): May 8, 2002
Copyright © 2002 American Chemical Society
*

 To whom correspondence should be addressed. E-mail:  dmacmill@ caltech.edu.

Abstract

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The first enantioselective catalytic direct cross-aldol reaction that employs nonequivalent aldehydes has been accomplished using proline as the reaction catalyst. Structural variation in both the aldol donor (R1 = Me, n-Bu, Bn, 91 to >99%) and aldol acceptor (R2 = I-Pr, I-Bu, c-C6H11, Et, Ph, 97−99% ee) are possible while maintaining high reaction efficiency (75−88% yield). Significantly, this new aldol variant allows facile enantioselective access to a broad range of β-hydroxy aldehydes which are valuable intermediates in polyketide syntheses.

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History

  • Published In Issue June 19, 2002
  • Received March 19, 2002

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