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Direct organocatalytic asymmetric aldol reactions of alpha-amino aldehydes: Expedient syntheses of highly enantiomerically enriched anti-beta-hydroxy-alpha-amino acids

Academic Article
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Overview

authors

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

publication date

  • September 2004

journal

  • Organic Letters  Journal

abstract

  • [reaction: see text] A simple and efficient method for the synthesis of highly enantiomerically enriched beta-hydroxy-alpha-amino acid derivatives has been developed. Direct asymmetric aldol reactions of a glycine aldehyde (aminoacetaldehyde) derivative have been performed under organocatalysis using l-proline or (S)-5-pyrrolidine-2-yl-1H-tetrazole. The reactions afforded anti-beta-hydroxy-alpha-amino aldehydes in good yield with high diastereoselectivity (dr up to >100:1) and high enantioselectivity (up to >99.5% ee), which were easily transformed into beta-hydroxy-alpha-amino acid derivatives.

subject areas

  • Aldehydes
  • Amino Acids
  • Catalysis
  • Indicators and Reagents
  • Molecular Structure
  • Proline
  • Stereoisomerism
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Identity

International Standard Serial Number (ISSN)

  • 1523-7060

Digital Object Identifier (DOI)

  • 10.1021/ol0485417

PubMed ID

  • 15387543
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Additional Document Info

start page

  • 3541

end page

  • 3544

volume

  • 6

issue

  • 20

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