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Organocatalytic Stereoselective Direct Aldol Reaction of Trifluoroethyl Thioesters
Author(s) -
Rossi Sergio,
Benaglia Maurizio,
Cozzi Franco,
Gei Andrea,
Benincori Tiziana
Publication year - 2011
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201100122
Subject(s) - chemistry , ketene , aldol reaction , thioester , thioacetal , stereoselectivity , lewis acids and bases , hypervalent molecule , organic chemistry , cationic polymerization , phosphine oxide , organocatalysis , chiral auxiliary , catalysis , combinatorial chemistry , enantioselective synthesis , acetal , phosphine , reagent , enzyme
The first organocatalytic, stereoselective and direct aldol reaction of activated thioesters with aldehydes has been accomplished. The trichlorosilyl ketene thioacetal generated in situ by adding a tertiary amine to a trifluoroethyl thioester in the presence of tetrachlorosilane is activated by catalytic amounts of an enantiomerically pure biheteroaromatic phosphine oxide to react with different aldehydes, coordinated to as well as activated by the chiral cationic hypervalent silicon species. Starting from a variety of readily available thioesters, this Lewis acid‐mediated Lewis base‐catalyzed transformation allows the direct synthesis of syn ‐β‐hydroxy thioesters in up to 95% ee .