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
收藏
页码：5752 / 5755
页数：4
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