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Stereoselective Nucleophilic Trifluoromethylation of N ‐( tert ‐Butylsulfinyl)imines by Using Trimethyl(trifluoromethyl)silane
Author(s) -
Prakash G. K. Surya,
Mandal Mihirbaran,
Olah George A.
Publication year - 2001
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 - 10.1002/1521-3773(20010202)40:3<589::aid-anie589>3.0.co;2-9
Subject(s) - stereoselectivity , trifluoromethylation , chemistry , nucleophile , silane , trifluoromethyl , nucleophilic addition , trimethylsilyl , yield (engineering) , medicinal chemistry , nucleophilic substitution , organic chemistry , catalysis , alkyl , materials science , metallurgy
A very general reaction is presented to achieve the nucleophilic transfer of “CF 3 ” to chiral N ‐( tert ‐butylsulfinyl)imines in high yield and high stereoselectivity (see reaction scheme). Tetrabutylammonium difluorotriphenylsilicate (TBAT) functions as a fluoride source, and aromatic, heterocyclic, and aliphatic sulfinylimines react smoothly. The high stereoselectivity suggests that the reaction proceeds through an open transition state. TMS=trimethylsilyl.