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A highly enantioselective route to either enantiomer of both alpha- and beta-amino acid derivatives

Academic Article
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Overview

authors

  • Cordova, A.
  • Watanabe, S.
  • Tanaka, F.
  • Notz, W.
  • Barbas III, Carlos

publication date

  • March 2002

journal

  • Journal of the American Chemical Society  Journal

abstract

  • This report describes the unprecedented use of unmodified aldehydes as donors in a catalytic asymmetric Mannich-type reaction. The proline-catalyzed reaction of N-PMP-protected alpha-imino ethyl glyoxylate with unmodified aliphatic aldehydes provided a general and very mild entry to either enantiomer of beta-amino and alpha-amino acids and derivatives in high yield and stereoselectivity. Six of the seven aldehydes studied yielded products with ee values of 99% or greater. The diastereoselectivity of the reaction increased with the bulkiness of the substituents of the aldehyde donor in the order R = Me < Et < i-Pr < n-Pent. In five of the cases studied, excellent syn stereoselectivities were achieved. In addition, the corresponding chiral beta-amino aldehyde adducts can be readily converted to the corresponding amino acid derivatives. Most significantly, this approach provides facile access to substituted beta-lactams.

subject areas

  • Amino Acids
  • Glyoxylates
  • Proline
  • Stereoisomerism
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Identity

International Standard Serial Number (ISSN)

  • 0002-7863

Digital Object Identifier (DOI)

  • 10.1021/ja017833p

PubMed ID

  • 11866595
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Additional Document Info

start page

  • 1866

end page

  • 1867

volume

  • 124

issue

  • 9

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