Why Do Some Fischer Indolizations Fail?

被引：44

作者：

Celebi-Oelcuem, Nihan ^{[1
]}

Boal, Ben W. ^{[1
]}

Huters, Alexander D. ^{[1
]}

Garg, Neil K. ^{[1
]}

Houk, K. N. ^{[1
]}

机构：

[1] Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2011年 / 133卷 / 15期

基金：

美国国家卫生研究院; 美国国家科学基金会;

关键词：

COPE REARRANGEMENTS; FACILE;

D O I：

10.1021/ja201035b

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The mechanisms of the Fischer indole synthesis and competing cleavage pathways were explored with SCS-MP2/6-31G(d) and aqueous solvation calculations. Electron-donating substituents divert the reaction pathway to heterolytic N-N bond cleavage and preclude the acid-promoted [3,3]-sigmatropic rearrangement.

引用

页码：5752 / 5755

页数：4

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