Probing the origin of carboxylate migration selectivity in Rh2(II)-catalyzed N-heterocycle formation from trisubstituted styryl azides

TETRAHEDRON LETTERS

卷:56

Article

Kong, Chen¹  Su, Naijing¹  Zhou, Fei¹  Jana, Navendu¹  Driver, Tom G.¹ 

[1] Univ Illinois, Dept Chem, Chicago, IL 60607 USA

关键词: Aryl azide;    Rhodium(II);    Indole;    Electrocyclization;    Migration;   

DOI  :  10.1016/j.tetlet.2015.01.008

来源: Elsevier

【 摘 要 】

Exposure of trisubstituted styryl azides to Rh-2(II)-carboxylate catalyst triggers a tandem 4 pi-electron-5atom electrocyclization-migration reaction. Herein we illustrate that the innate preference for selectivity of the carboxylate migration to form 3H-indoles can be overcome by steric pressure to produce only 1,2,3-trisubstituted indoles. (C) 2015 Published by Elsevier Ltd.

【 授权许可】

Free