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A Convenient Enantioselective Synthesis of (S)-α-Trifluoromethylisoserine

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posted on 08.07.2005, 00:00 by Alberto Avenoza, Jesús H. Busto, Gonzalo Jiménez-Osés, Jesús M. Peregrina
This report describes two straightforward synthetic methodologies to obtain α-CF3-isoserine, a new α,α-disubstituted β-amino acid, from α-(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.