Synthesis of optically active constrained 2-substituted norstatines: a straightforward application of Seebach's "SRS" synthetic principle

Arturo Battaglia; Andrea Guerrini; Carlo Bertucci

doi:10.1021/jo0486793

Synthesis of optically active constrained 2-substituted norstatines: a straightforward application of Seebach's "SRS" synthetic principle

J Org Chem. 2004 Dec 24;69(26):9055-62. doi: 10.1021/jo0486793.

Authors

Arturo Battaglia¹, Andrea Guerrini, Carlo Bertucci

Affiliation

¹ Istituto CNR per la Sintesi Organica e Fotoreattività I.S.O.F., Area della Ricerca di Bologna, via P. Gobetti 101, 40129 Bologna, Italy. battaglia@isof.cnr.it

PMID: 15609938
DOI: 10.1021/jo0486793

Abstract

A straightforward two-step methodology of synthesis of optically active (2R)-substituted norstatines via addition of N-tert-butoxycarbonyl-substituted aldimines to (2S)-chiral enolates of 1,3-dioxolan-4-ones has been developed. In particular, the use of the natural (2S)-malic acid is examined for the synthesis of potential GABAergic spirocyclic gamma-lactams.