Synthesis 2004(17): 2910-2918  
DOI: 10.1055/s-2004-831256
PAPER
© Georg Thieme Verlag Stuttgart · New York

A Highly Efficient Asymmetric Synthesis of Homotaurine Derivatives via Diastereoselective Ring-Opening of γ-Sultones

Dieter Enders*, Wacharee Harnying
Institut für Organische Chemie, Rheinisch-Westfälische Technische Hochschule, Professor-Pirlet-Str. 1, 52074 Aachen, Germany
Fax: +49(241)8092127; e-Mail: Enders@rwth-aachen.de;
Further Information

Publication History

Received 23 July 2004
Publication Date:
07 October 2004 (online)

Abstract

A highly efficient asymmetric synthesis of α,γ-substituted γ-amino sulfonates via diastereoselective ring-opening of enantiopure α,γ-substituted γ-sultones with inversion of configuration at the attacked γ-carbon is described. In the key step sodium azide is used as the nucleophilic nitrogen source. Secondary and tertiary γ-amino sulfonates were synthesized in very good yields and excellent diastereo- and enantiomeric excesses (de, ee ≥98%).