Harnessing the Electrophilicity of Keteniminium Ions: A Simple and Straightforward Entry to Tetrahydropyridines and Piperidines from Ynamides

被引：81

作者：

Lecomte, Morgan ^{[1
]}

Evano, Gwilherm ^{[1
]}

机构：

[1] Univ Libre Bruxelles, Chim Organ Lab, Serv Chim & PhysicoChim Organ, Ave FD Roosevelt 50,CP160-06, B-1050 Brussels, Belgium

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2016年 / 55卷 / 14期

关键词：

cationic cyclizations; hydride shift; keteniminium ions; piperidines; ynamides; H BOND FUNCTIONALIZATION; ASTERISK-ASTERISK; SUBSTITUTED YNAMIDES; ORGANIC-SYNTHESIS; CYCLIZATION; AMIDES; REARRANGEMENTS; ALKYNES; 1,1-DIBROMO-1-ALKENES; TETRAHYDROQUINOLINES;

D O I：

10.1002/anie.201510729

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An efficient, modular and straightforward entry to tetrahydropyridines and piperidines is reported. This reaction is based on a formal intramolecular hydroalkylation of readily available, properly substituted ynamides which, upon simple activation under acidic conditions, generate highly reactive activated keteniminium ions whose reactivity can be finely controlled to induce a remarkably efficient [1,5]-hydride shift from unactivated C-H bonds and trigger a cationic cyclization which is complete within minutes.

引用

页码：4547 / 4551

页数：5

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