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

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: [phone].