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Highly Stereoselective Trichloromethylation of N ‐( tert ‐Butylsulfinyl)aldimines: Facile Synthesis of Chiral α‐Trichloromethylamines
Author(s) -
Li Ya,
Cao Yunlv,
Gu Jiaying,
Wang Wei,
Wang Han,
Zheng Tao,
Sun Zhihua
Publication year - 2011
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201001495
Subject(s) - aldimine , stereoselectivity , chemistry , enantioselective synthesis , nucleophilic addition , nucleophile , stereochemistry , medicinal chemistry , organic chemistry , catalysis
The first highly stereoselective and facile synthesis ofα‐trichloromethylamines is described by using a nucleophilic trichloromethylation strategy. With tetrabutylammonium triphenyldifluorosilicate (TBAT) as the mediator, the trichloromethyl anion (CCl 3 – ) from TMSCCl 3 can be transferred to N ‐( tert ‐butylsulfinyl)aldimines in excellent yields and with high diastereoselectivity (≥99:1 dr ).