Department of Chemistry, University of Michigan, Ann Arbor, Michigan 48109, United States.
Org Lett. 2022 Jun 24;24(24):4344-4348. doi: 10.1021/acs.orglett.2c01483. Epub 2022 Jun 14.
Detailed herein is the development of a photochemical 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.
本文详细介绍了在光照条件下，环丙基亚胺与取代烯烃之间的光化学分子间[3+2]环加成反应，生成氨基环戊烷衍生物。环丙基亚胺的席夫碱设计为能够实现掩蔽的 N 中心自由基途径，其中在可见光激发下实现所需的开壳层特性。通过溶剂解和 N-酰化，环加成产物可直接转化为 N-官能化的氨基环戊烷。该反应序列的光化学反应部分被证明可在连续流中进行。
