Asymmetric synthesis of homochiral differentially protected bis-β-amino acid scaffolds

Steven D. Bull, Stephen G. Davies*, Paul M. Roberts, Edward D. Savory, Andrew D. Smith

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

28 Citations (Scopus)

Abstract

A strategy for the asymmetric synthesis of homochiral [(R,R)- or (S,S)-], or meso-(R,S) bis-β-amino acid scaffolds, formally resulting from the stepwise conjugate addition of two differentially protected homochiral lithium amides to two α,β-unsaturated esters attached to a central arene, is demonstrated. Further manipulation enables the efficient synthesis of orthogonally protected pseudo-meso or pseudo-C2 symmetric scaffolds via selective N-benzyl or N-allyl deprotection, enabling regio-, stereo- and chemoselective functionalisation.

Original languageEnglish
Pages (from-to)4629-4642
Number of pages14
JournalTetrahedron
Volume58
Issue number23
DOIs
Publication statusPublished - 3 Jun 2002

Keywords

  • Asymmetric synthesis
  • Conjugate addition
  • Differential deprotection
  • Lithium amides

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