Synthesis of chiral β2,2,3-3-amino-2-hydroxyalkanoates and 3-alkyl-3-hydroxy-β-lactams by double asymmetric induction

Andrea Guerrini, Greta Varchi, Rizzo Daniele, Cristian Samorì, Arturo Battaglia

Research output: Contribution to journalArticlepeer-review

15 Scopus citations

Abstract

Reactions of chiral (2S)-enolates of dioxolan-4-ones, derived from lactic, mandelic, and phenyllactic acids, with aliphatic (SS)- and (SR)-tert-butylsulfinyl aldimines afforded conformationally restrained C2-disubstituted N,O-orthogonally protected 3-amino-2-hydroxyalkanoates in the form of N-sulfinyl protected 1′-aminodioxolan-4-ones. The product distribution showed that there is significant kinetic selectivity, due to the presence of 'matched' and 'mismatched' components, between the (S)- or (R)-tert-butylsulfinyl aldimines and the (2S)-enolates of the 1,3-dioxolan-4-ones. Selective methoxide-induced removal of the acetal group of the N-sulfinyl-1′-aminodioxolanones yielded the corresponding N-sulfinyl protected methyl alkanoates. In addition, the selective acid-induced removal of the sulfinyl group of the N-sulfinyl-1′-aminodioxolanones provided the corresponding N-unprotected 1′-aminodioxolanones, whose base-induced cyclization afforded the corresponding β-lactams.

Original languageEnglish (US)
Pages (from-to)7949-7969
Number of pages21
JournalTetrahedron
Volume63
Issue number33
DOIs
StatePublished - Aug 13 2007

Keywords

  • 3-Hydroxy-β-lactams
  • Aldimines
  • Dioxolan-4-ones
  • Double asymmetric induction
  • α-Hydroxy-β-amino acids

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Fingerprint

Dive into the research topics of 'Synthesis of chiral β<sup>2,2,3</sup>-3-amino-2-hydroxyalkanoates and 3-alkyl-3-hydroxy-β-lactams by double asymmetric induction'. Together they form a unique fingerprint.

Cite this