Asymmetric Synthesis of a-Mercapto-b-Amino Acid Derivatives: Application to the Synthesis of Polysubstituted Thiomorpholines

J L Candela-Lena, S G Davies, P M Roberts, B Roux, A J Russell, E M Sanchez-Fernandez, Andrew David Smith, . .

Research output: Contribution to journalArticlepeer-review

18 Citations (Scopus)

Abstract

Tandem conjugate addition of homochiral lithium N-benzyl-N-(alpha-methyl-p-methoxybenzyl)amide to tert-butyl cinnamate and enolate trapping with (TsSBu)-Bu-t proceeds with high diastercoselectivity to give a homochiral anti-alpha-tert-butylthio-beta-amino ester. Stepwise deprotection gives the corresponding free alpha-tert-butylthio-beta-amino acid without epimerisation. Tandem conjugate addition of homochiral lithium N-allyl-N-(alpha-methylbenzyl)amide to tert-butyl cinnamate and enolate trapping with TsS'Bu followed by conversion of the S-tert-butyl group to a disulphide, and reduction with Lalancette's reagent generates polysubstituted thiomorpholine derivatives. (c) 2006 Elsevier Ltd. All rights reserved.

Original languageEnglish
Pages (from-to)1135
Number of pages1135
JournalTetrahedron: Asymmetry
Volume17
DOIs
Publication statusPublished - 3 Apr 2006

Keywords

  • NEUROTOXIN TYPE-B
  • POTENT INHIBITORS
  • ALLYLIC AMINES
  • AMMONIA EQUIVALENTS
  • CONJUGATE ADDITION
  • ORGANIC-SYNTHESIS
  • PROTECTING GROUP
  • PROTONATION
  • CLEAVAGE
  • EXCHANGE

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