The first synthesis of N,O-protected β2,2,3,3-isoserines bearing two adjacent quaternary stereogenic centers and their corresponding β-lactams

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

Research output: Contribution to journalArticle

16 Scopus citations

Abstract

The reaction of chiral (2S)-enolates of dioxolan-4-ones, derived from lactic and mandelic acids, with (SR)-tert-butyl sulfinyl ketimines, derived from butan-2-one, pentan-2-one, and decan-2-one, afforded conformationally restrained β2,2,3,3-isoserines bearing two adjacent quaternary stereogenic centers in the form of N-sulfinyl protected 1′-amino-dioxolan-4-ones. The selective acid-induced removal of the sulfinyl protecting group provided the corresponding 1′-aminodioxolanones, whose base-induced cyclization afforded the corresponding chiral tetra-substituted 3-hydroxy-β-lactams. The synthesis of a dipeptide by reaction coupling between the 1′-aminodioxolanone (2S,5R,1′R)-19 and N,N-dimethylglycine was successfully achieved.

Original languageEnglish (US)
Pages (from-to)5081-5085
Number of pages5
JournalTetrahedron Letters
Volume48
Issue number29
DOIs
StatePublished - Jul 16 2007

Keywords

  • Tetrasubstituted 3-hydroxy-β-lactams
  • Tetrasubstituted β-isoserines
  • α-Hydroxy-β-amino acids
  • β-Peptides

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Fingerprint Dive into the research topics of 'The first synthesis of N,O-protected β<sup>2,2,3,3</sup>-isoserines bearing two adjacent quaternary stereogenic centers and their corresponding β-lactams'. Together they form a unique fingerprint.

Cite this