N ‐Trifluoromethylthiophthalimide: A Stable Electrophilic SCF 3 ‐Reagent and its Application in the Catalytic Asymmetric Trifluoromethylsulfenylation | Zendy

Bootwicha Teerawut | Zendy; Liu Xiangqian | Zendy; Pluta Roman | Zendy; Atodiresei Iuliana | Zendy; Rueping Magnus | Zendy

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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.

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