Synthesis 2005(11): 1807-1816  
DOI: 10.1055/s-2005-865326
PAPER
© Georg Thieme Verlag Stuttgart · New York

Asymmetric Synthesis of cis-3,4-Disubstituted β-Sultams

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

Publication History

Received 20 January 2005
Publication Date:
18 April 2005 (online)

Abstract

The asymmetric synthesis of cis-3,4-disubstituted β-sultams is reported. The protocol is based on the oxidation of 1,2-aminothiols with H2O2 and ammonium heptamolybdate. The chlorination of the resulting β-amino sulfonic acids was achieved utilising a solution of phosgene in toluene. The β-aminosulfonyl chlorides obtained were cyclised to the title compounds under basic conditions without epimerisation (de, ee ≥96%) and good overall yields (17-59%). In addition, the N-Cbz-protection of β-sultams was easily accomplished.