Journal of Organic Chemistry 2005-07-08

A convenient enantioselective synthesis of (S)-alpha-trifluoromethylisoserine.

Alberto Avenoza, Jesús H Busto, Gonzalo Jiménez-Osés, Jesús M Peregrina

Index: J. Org. Chem. 70(14) , 5721-4, (2005)

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Abstract

[reaction: see text] This report describes two straightforward synthetic methodologies to obtain alpha-CF3-isoserine, a new alpha,alpha-disubstituted beta-amino acid, from alpha-(trifluoromethyl)acrylic acid. The routes involve the synthesis of five-membered cyclic sulfates (using sulfuryl chloride) or sulfamidates (using the Burgess reagent) from the corresponding chiral diols, which are obtained by a catalytic asymmetric dihydroxylation (AD) reaction.