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The Combination of TsNH 2 and NCS as Nitrogen and Chlorine Sources for Direct Diamination of Enones
Author(s) -
Timmons Cody,
Chen Dianjun,
Xu Xin,
Li Guigen
Publication year - 2003
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.200300326
Subject(s) - chemistry , electrophile , nucleophile , nitrogen , ring (chemistry) , chlorine , regioselectivity , combinatorial chemistry , amination , chlorine atom , medicinal chemistry , organic chemistry , catalysis
The regio‐, stereo‐, and chemoselective diamination of enones has been achieved without the observation of any haloamines. The reaction employs the readily available inexpensive combination of NCS and TsNH 2 as an electrophilic nitrogen source, and three nitriles as nucleophilic nitrogen sources. A novel mechanism involving the formation of aziridinium intermediates from the reaction of TsNHCl with olefins and a new [2+3] cyclic addition for aziridinim ring opening has been proposed for the electrophilic diamination of olefins. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)