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Asymmetric synthesis of quaternary alpha- and beta-amino acids and beta-lactams via proline-catalyzed mannich reactions with branched aldehyde donors

Academic Article
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Overview

authors

  • Chowdari, N. S.
  • Suri, J. T.
  • Barbas III, Carlos

publication date

  • July 2004

journal

  • Organic Letters  Journal

abstract

  • [reaction: see text] L-Proline-catalyzed direct asymmetric Mannich reactions of N-PMP protected alpha-imino ethyl glyoxylate with various alpha,alpha-disubstituted aldehydes affords quaternary beta-formyl alpha-amino acid derivatives with excellent yields and enantioselectivities. The Mannich products are further converted to the corresponding quaternary alpha- and beta-amino acids and beta-lactams.

subject areas

  • Aldehydes
  • Amino Acids
  • Catalysis
  • Combinatorial Chemistry Techniques
  • Crystallography, X-Ray
  • Molecular Conformation
  • Molecular Structure
  • Proline
  • Stereoisomerism
  • beta-Lactams
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Identity

International Standard Serial Number (ISSN)

  • 1523-7060

Digital Object Identifier (DOI)

  • 10.1021/ol049248

PubMed ID

  • 15255677
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Additional Document Info

start page

  • 2507

end page

  • 2510

volume

  • 6

issue

  • 15

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