Asymmetric Synthesis of 1,2-anti-Disubstituted Taurine Derivatives

Dieter Enders; Dirk Iffland; Gerhard Raabe

doi:10.1055/s-0029-1216643

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Synthesis 2009(10): 1683-1688
DOI: 10.1055/s-0029-1216643

PAPER

Asymmetric Synthesis of 1,2-anti-Disubstituted Taurine Derivatives

Dieter Enders*, Dirk Iffland, Gerhard Raabe
Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany
Fax: +49(241)8092127; e-Mail: enders@rwth-aachen.de;

Further Information

Publication History

Received 12 February 2009
Publication Date:
14 April 2009 (online)

Abstract
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Abstract

An efficient asymmetric synthesis of anti-1,2-disubstituted taurine derivatives through nucleophilic addition of phenylmethanesulfonate to various N-acylimines in the presence of 1,2:5,6-di-O-isopropylidene-α-d-allofuranose as a chiral auxiliary is described. The taurine derivatives were obtained in three steps with good overall yields (36-61%) and excellent enantiomeric excesses (83-98%). The diastereomeric excesses of 15-91% could be improved to 90-98% by column chromatography or recrystallization. The relative and absolute configurations of the products were determined by means of an X-ray crystal structure analysis.

Key words

taurine - asymmetric synthesis - sugar auxiliary - N-acylimines - α-amido sulfones - chiral auxiliary

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CCDC 713539 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from www.ccdc.cam.ac.uk/data_request/cif or by contacting the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK: fax: +44(1223)336033.