Doubly diastereoselective conjugate addition of enantiopure lithium amides to enantiopure N-enoyl oxazolidin-2-ones: a mechanistic probe

Stephen G. Davies, Ai M. Fletcher, Gesine J. Hermann, Giovanna Poce, Paul M. Roberts, Andrew D. Smith, Miles J. Sweet, James E. Thomson, Andrew David Smith

Research output: Contribution to journalArticlepeer-review

21 Citations (Scopus)

Abstract

The doubly diastereoselective conjugate addition of the antipodes of lithium N-benzyl-N-(alpha-methylbenzyl)amide to a range of enantiopure N-enoyl oxazolidin-2-ones has been used as a mechanistic probe to determine that the reactive conformation is the anti-s-cis form. The beta-amino carbonyl products resulting from these conjugate addition reactions are useful templates for further elaboration into an alpha,beta,alpha-pseudotripeptide. (C) 2010 Elsevier Ltd. All rights reserved.

Original languageEnglish
Pages (from-to)1635-1648
Number of pages14
JournalTetrahedron: Asymmetry
Volume21
Issue number13-14
DOIs
Publication statusPublished - 14 Jul 2010

Keywords

  • PARALLEL KINETIC RESOLUTION
  • HOMOCHIRAL ALPHA,BETA-UNSATURATED ESTERS
  • JASPINE-B PACHASTRISSAMINE
  • PARTIALLY-MODIFIED RETRO
  • D-LYXO-PHYTOSPHINGOSINE
  • BETA-AMINO ACIDS
  • ASYMMETRIC-SYNTHESIS
  • ORGANOCOPPER REAGENTS
  • MICHAEL ADDITIONS
  • ORGANIC-SYNTHESIS

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