A Convenient Enantioselective Synthesis of (S)-alfa-Trifluoromethylisoserine
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Universidad de La Rioja
info
ISSN: 0022-3263
Year of publication: 2005
Volume: 70
Issue: 14
Pages: 5721-5724
Type: Article
More publications in: Journal of Organic Chemistry
Abstract
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. © 2005 American Chemical Society.