A One-Pot Photochemical Method for the Generation of Functionalized Aminocyclopentanes

被引：14

作者：

Collins, James L., III ^{[1
]}

Staveness, Daryl ^{[1
]}

Sowden, Madison J. ^{[1
]}

Stephenson, Corey R. J. ^{[1
]}

机构：

[1] Univ Michigan, Dept Chem, Ann Arbor, MI 48109 USA

来源：

ORGANIC LETTERS | 2022年 / 24卷 / 24期

基金：

美国国家卫生研究院;

关键词：

D O I：

10.1021/acs.orglett.2c01483

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Detailed herein is the development of a photo-chemical intermolecular formal [3+2] cycloaddition between cyclopropylimines and substituted alkenes to generate aminocyclopentane derivatives. The Schiff base of the cyclopropylimine was designed to enable a masked N-centered radical approach in which the requisite open-shell character was achieved upon excitation with visible light. The cycloaddition products were directly converted to N-functionalized aminocyclopentanes via solvolysis and N-acylation. The photochemical component of this reaction sequence was demonstrated to operate in continuous flow.

引用

页码：4344 / 4348

页数：5

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