Imidomethylation of C-nucleophiles using O-phthalimidomethyl trichloroacetimidate and catalytic amounts of TMSOTf

被引：25
作者：
Ali, IAI
El Ashry, ESH
Schmidt, RR
机构：
[1] Univ Konstanz, Dept Chem, D-78457 Constance, Germany
[2] Univ Alexandria, Fac Sci, Dept Chem, Alexandria, Egypt
来源：
TETRAHEDRON | 2004年 / 60卷 / 22期
关键词：
D O I：
10.1016/j.tet.2004.04.011
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The O-phthalimidomethyl trichloroacetimidate (1), as a latent aminomethylating agent, exhibits high electrophilicity towards a variety of C-nucleophiles in the presence of catalytic amounts of TMSOTf and mild reaction conditions. The nucleophiles include aromatics, alkenes and active methylene compounds 2-11 whereby a phthalimidomethyl group could be introduced to give compounds 12-22. Removal of the phthaloyl group gave the respective amines, beta-amino ketones, and beta-amino acids. The O-(trichloroacetamido)methyl trichloroacetimidate (35) was also found to be a good amidomethylating agent. (C) 2004 Elsevier Ltd. All rights reserved.
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收藏
页码：4773 / 4780
页数：8
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