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N ‐Trifluoromethylthiophthalimide: A Stable Electrophilic SCF 3 ‐Reagent and its Application in the Catalytic Asymmetric Trifluoromethylsulfenylation
Author(s) -
Bootwicha Teerawut,
Liu Xiangqian,
Pluta Roman,
Atodiresei Iuliana,
Rueping Magnus
Publication year - 2013
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201304957
Subject(s) - enantioselective synthesis , electrophile , stereocenter , catalysis , reagent , chemistry , cinchona , yield (engineering) , organic chemistry , combinatorial chemistry , materials science , metallurgy
Cinchona alkaloid catalysts in combination with air‐ and moisture‐stable N ‐trifluoromethylthiophthalimide as electrophilic SCF 3 source enabled the catalytic enantioselective trifluoromethylsulfenylation. Thus, a series of α‐SCF 3 esters that bear a quaternary carbon stereogenic center were obtained with excellent yield and enantioselectivity. Moreover, the products can be readily converted into valuable α‐SCF 3 β‐hydroxyesters.