Transposed Paterno-Buchi Reaction

被引：40
|
作者：
Kumarasamy, Elango [1 ]
Raghunathan, Ramya [1 ]
Kandappa, Sunil Kumar [1 ]
Sreenithya, A. [2 ]
Jockusch, Steffen [3 ]
Sunoj, Raghavan B. [2 ]
Sivaguru, J. [1 ]
机构：
[1] North Dakota State Univ, Dept Chem & Biochem, Fargo, ND 58108 USA
[2] Indian Inst Technol, Dept Chem, Bombay 400076, Maharashtra, India
[3] Columbia Univ, Dept Chem, New York, NY 10027 USA
来源：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2017年 / 139卷 / 02期
关键词：
NON-BIARYL ATROPISOMERS; PHOTOCHEMICAL-REACTIONS; PHOTOASSISTED SYNTHESIS; 2+2 PHOTOCYCLOADDITION; CARBONYL-COMPOUNDS; ALPHA-OXOAMIDES; CHIRALITY; TRANSFORMATIONS; PHOTOREACTIONS; CYCLOADDITION;
D O I：
10.1021/jacs.6b05936
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A complementary strategy of utilizing pi pi* excited state of alkene instead of n pi* excited state of the carbonyl chromophore in a "transposed Paterno-Buchi" reaction is evaluated with atropisomeric enamides as the model system. Based on photophysical investigations, the nature of excited states and the reactive pathway was deciphered leading to atropselective reaction. This new concept of switching of excited state configuration should pave the way to control the stereochemical course of photoreaction due to the orbital approaches required for photochemical reactivity.
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页码：655 / 662
页数：8
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