Highly Stereoselective Trichloromethylation of  N ‐( tert ‐Butylsulfinyl)aldimines: Facile Synthesis of Chiral α‐Trichloromethylamines | Zendy

Li Ya | Zendy; Cao Yunlv | Zendy; Gu Jiaying | Zendy; Wang Wei | Zendy; Wang Han | Zendy; Zheng Tao | Zendy; Sun Zhihua | Zendy

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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 ).

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