Asymmetric synthesis of β-substituted γ-lactams via rhodium/diene-catalyzed 1,4-additions: application to the synthesis of (R)-baclofen and (R)-rolipram

Org Lett. 2011 Feb 18;13(4):788-91. doi: 10.1021/ol103054a. Epub 2011 Jan 19.

Abstract

An efficient rhodium/diene-catalyzed asymmetric addition of arylboronic acids to α,β-unsaturated γ-lactams has been developed. The power of this methodology is further demonstrated by the concise synthesis of (R)-baclofen and (R)-rolipram.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Baclofen / chemical synthesis*
  • Baclofen / chemistry
  • Boronic Acids / chemistry*
  • Catalysis
  • Molecular Structure
  • Rhodium / chemistry*
  • Rolipram / chemical synthesis*
  • Rolipram / chemistry
  • Stereoisomerism
  • beta-Lactams / chemical synthesis*
  • beta-Lactams / chemistry

Substances

  • Boronic Acids
  • beta-Lactams
  • Rhodium
  • Baclofen
  • Rolipram