Enantioselective hydrogenation of alpha-aminomethylacrylates containing a free NH group for the synthesis of beta-amino acid derivatives

Proc Natl Acad Sci U S A. 2007 Oct 23;104(43):16787-92. doi: 10.1073/pnas.0704461104. Epub 2007 Oct 17.

Abstract

We describe highly enantioselective synthesis of beta-amino acid derivatives (1a-c) using asymmetric hydrogenation of alpha-aminomethylacrylates (2a-c), which contain a free basic N H group, as the key step. The alpha-aminomethylacrylates (2a-c) were prepared using the Baylis-Hillman reaction of an appropriate aldehyde with methyl acrylate followed by acetylation of the resulting allylic alcohols (4a-b) and S(N)2'-type amination of the allylic acetates (3a-b).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acids / chemical synthesis*
  • Catalysis
  • Hydrogenation
  • Methacrylates / chemical synthesis*
  • Methacrylates / chemistry*
  • Stereoisomerism

Substances

  • Amino Acids
  • Methacrylates