Enantiospecific Photochemical Norrish/Yang Type II Reaction of Nonbiaryl Atropchiral α-Oxoamides in Solution-Axial to Point Chirality Transfer

被引：61

作者：

Ayitou, Anoklase Jean-Luc ^{[1
]}

Jesuraj, Josepha L. ^{[1
]}

Barooah, Nilotpal ^{[1
]}

Ugrinov, Angel ^{[1
]}

Sivaguru, J. ^{[1
]}

机构：

[1] N Dakota State Univ, Dept Chem & Mol Biol, Fargo, ND 58105 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2009年 / 131卷 / 32期

基金：

美国国家科学基金会;

关键词：

ASYMMETRIC INDUCTION; AMIDES; PHOTOCYCLIZATION; AUXILIARY; LIGANDS; LACTAM; RING;

D O I：

10.1021/ja9050586

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

alpha-Oxoamides 1 with o-tert-butyl substitution on the N-phenyl moiety were found to be stable axially chiral atropisomers. These axially chiral alpha-oxoamides undergo enantiospecific photochemical gamma-Hydrogen abstraction in CHCl3 to yield beta-lactams with high enantioselectivity (e.r. similar to 90:10) in solution. The extent of enantioselectivity was found to be dependent on the reaction temperature.

引用

页码：11314 / +

页数：4

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