Highly Diastereoselective Synthesis of 5/6-Fused Bicyclic Ring Systems via Radical Cyano Group Migration

被引：0

作者：

Wu, Chenxi ^{[1
,2
]}

Wu, Dan-Yang ^{[1
,2
]}

Wang, Yu-Hao ^{[1
,2
]}

Wang, Pu-Sheng ^{[1
,2
]}

机构：

[1] Univ Sci & Technol China, Hefei Natl Res Ctr Phys Sci Microscale, Hefei 230026, Anhui, Peoples R China

[2] Univ Sci & Technol China, Dept Chem, Hefei 230026, Anhui, Peoples R China

来源：

ORGANIC LETTERS | 2025年 / 27卷 / 10期

基金：

中国国家自然科学基金;

关键词：

INTERMOLECULAR 2+2 PHOTOCYCLOADDITION; PHOTOCHEMICAL-REACTIONS; CYCLIZATION; CATALYSIS; COMBINATION; LIGHT;

D O I：

10.1021/acs.orglett.5c00270

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Here we report a highly diastereoselective cyano group transfer radical cyclization reaction to construct 5/6-fused bicyclic ring systems that bear three contiguous and congested stereogenic elements, with 100% atom economy under catalyst-free and near-ultraviolet light irradiation conditions. Mechanistic investigations and density functional theory calculations suggest that the diastereoselectivity is governed by the conformational distribution of the triplet diradical intermediate and the rate of reverse intersystem crossing (RISC) before radical coupling.

引用

页码：2406 / 2411

页数：6

共 40 条

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