Parallel synthesis of homochiral beta-amino acids

Stephen G. Davies, Andrew W. Mulvaney, Angela J. Russell, Andrew D. Smith

Research output: Contribution to journalArticlepeer-review

47 Citations (Scopus)

Abstract

The parallel asymmetric synthesis of an array of 30 P-amino acids of high enantiomeric purity using the conjugate addition of homochiral lithium N-benzyl-N-(alpha-methylbenzyl)amide as the key step is accomplished. The experimental simplicity and highly practical nature of the protocol is demonstrated by the efficient parallel conversion of 15 alpha,beta-unsaturated esters to both enantiomeric series of the corresponding beta-amino acids in high overall yields and selectivities with minimal purification involved in each step of the reaction protocol. (C) 2007 Elsevier Ltd. All rights reserved.

Original languageEnglish
Pages (from-to)1554-1566
Number of pages13
JournalTetrahedron: Asymmetry
Volume18
Issue number13
DOIs
Publication statusPublished - 17 Jul 2007

Keywords

  • SOLID-PHASE SYNTHESIS
  • ENANTIOSELECTIVE SYNTHESIS
  • ASYMMETRIC-SYNTHESIS
  • ORGANIC-SYNTHESIS
  • SMALL MOLECULES
  • ALDOL REACTIONS
  • IRON COMPLEXES
  • LITHIUM AMIDES
  • DERIVATIVES
  • LIBRARY

Fingerprint

Dive into the research topics of 'Parallel synthesis of homochiral beta-amino acids'. Together they form a unique fingerprint.

Cite this