Synthesis of α2,23-diamino acids by double stereodifferentiation aldol addition of oxazolidinone enolates to N-(tert-butylsulfinyl) imines

Andrea Guerrini, Greta Varchi, Cristian Samorì, Arturo Battaglia

Research output: Contribution to journalArticle

9 Scopus citations

Abstract

A novel application of Seebach's "SRS" synthetic principle works efficiently when conformationally restrained trisubstituted chiral α2,23-diamino acids are synthesized by double stereoinduction reactions of chiral oxazolidinone enolates with N-sulfinyl aldimines. Two stereoisomers were isolated in a form of 1′-(sulfinylamino) oxazolidinones and bicyclic 1H,3H-imidazo[1,5-c]oxazole-1,5(6H)-diones, from which the α2,23-diamino acids are obtained by selective deprotection methodologies. Among a variety of highly functionalized diamino acids, this highly diastereoselective protocol provides a synthetic route for yet unreported C-glycosyl and α-nucleoside diamino acids.

Original languageEnglish (US)
Pages (from-to)3834-3844
Number of pages11
JournalEuropean Journal of Organic Chemistry
Issue number22
DOIs
StatePublished - Aug 1 2008

Keywords

  • Amino acids
  • Antifungal agents
  • Diastereoselectivity
  • Nitrogen heterocycles
  • Oxygen heterocycles
  • Peptidomimetics

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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