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Direct asymmetric organocatalytic michael reactions of alpha,alpha-disubstituted aldehydes with beta-nitrostyrenes for the synthesis of quaternary carbon-containing products

Academic Article
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Overview

authors

  • Mase, N.
  • Thayumanavan, R.
  • Tanaka, F.
  • Barbas III, Carlos

publication date

  • July 2004

journal

  • Organic Letters  Journal

abstract

  • [reaction: see text] Direct asymmetric catalytic Michael reactions have been performed using chiral-amine/acid bifunctional catalysts. Performed with 0.3 equiv of (S)-(+)-1-(2-pyrrolidinylmethyl)pyrrolidine and 0.3 equiv of trifluoroacetic acid as the catalyst, the reaction of alpha,alpha-dialkylaldehydes with (E)-beta-nitrostyrene provided the alpha,alpha-dialkyl Michael products in up to 96% yield with up to 91% ee. With respect to enantioselectivity, l-proline was a poor catalyst of this class of Michael reactions.

subject areas

  • Aldehydes
  • Amines
  • Carbon
  • Catalysis
  • Molecular Structure
  • Proline
  • Spectrometry, Fluorescence
  • Stereoisomerism
  • Styrenes
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Identity

International Standard Serial Number (ISSN)

  • 1523-7060

Digital Object Identifier (DOI)

  • 10.1021/ol049196o

PubMed ID

  • 15255682
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Additional Document Info

start page

  • 2527

end page

  • 2530

volume

  • 6

issue

  • 15

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