A convenient enantioselective synthesis of (S)-alpha-trifluoromethylisoserine.
[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.
Avenoza
Alberto
A
Departamento de Química, Universidad de La Rioja, Grupo de Síntesis Química de La Rioja, U.A.-C.S.I.C., E-26006 Logroño, Spain. alberto.avenoza@dq.unirioja.es
Busto
Jesús H
JH
Jiménez-Osés
Gonzalo
G
Peregrina
Jesús M
JM
D002384:Catalysis; D005231:Fatty Acids, Unsaturated / Q000138:chemical synthesis*; D008956:Models, Chemical; D012694:Serine / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D013237:Stereoisomerism; D013441:Sulfinic Acids / Q000737:chemistry; D013449:Sulfonamides / Q000737:chemistry; D043823:Taxoids / Q000138:chemical synthesis / Q000494:pharmacology; D047090:beta-Lactams / Q000138:chemical synthesis / Q000494:pharmacology
D005231:Fatty Acids, Unsaturated; D013441:Sulfinic Acids; D013449:Sulfonamides; D043823:Taxoids; D047090:beta-Lactams; C503221:methyl (R,E)-(-)-tetradeca-2,4,5-trienoate; D012694:Serine; C072421:isoserine; C044255:sulfonyl chloride