Asymmetric synthesis of α-amino carbonyls (aldehydes, ketones and acids) using lithium (R)-N-benzyl-N-α-methylbenzylamide

S. G. Davies*, S. W. Epstein, O. Ichihara, A. D. Smith

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

11 Citations (Scopus)

Abstract

The diastereoselective conjugate addition of lithium (R)-N-benzyl-N-α-methylbenzylamide to α,β-unsaturated esters and subsequent enolate hydroxylation, followed by reduction and oxidative cleavage provides a facile route to N,N-protected α-amino aldehydes and ketones. Further manipulation furnishes α-amino acids in high enantiomeric excess.

Original languageEnglish
Pages (from-to)1599-1601
Number of pages3
JournalSynlett
Issue number10
DOIs
Publication statusPublished - 1 Jan 2001

Keywords

  • Asymmetric synthesis
  • Conjugate addition
  • Lithium amides
  • α-amino acid
  • α-amino aldehyde
  • β-amino acids

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