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.
