Iridium-Catalyzed [4+3] Cyclization of ortho-Tosylaminophenyl-Substituted para-Quinone Methides with Vinylic Oxiranes/Vinyl Aziridines

被引：3

作者：

Wang, Junwei ^{[1
]}

Zhao, Lin ^{[1
]}

Li, Caihong ^{[1
]}

Zhao, Lei ^{[1
]}

Zhao, Kun ^{[1
]}

Hu, Yang ^{[1
]}

Hu, Lihong ^{[1
]}

机构：

[1] Nanjing Univ Chinese Med, Jiangsu Key Lab Funct Subst Chinese Med, Sch Pharm, Nanjing, Peoples R China

来源：

ASIAN JOURNAL OF ORGANIC CHEMISTRY | 2021年 / 10卷 / 08期

基金：

中国国家自然科学基金;

关键词：

4+3] Cyclization; para-Quinone Methides; Vinylic Oxiranes; Vinyl Aziridines; REGIOSELECTIVE 3+2 CYCLOADDITION; RING-OPENING CYCLIZATION; DIVERGENT SYNTHESIS; ENANTIOSELECTIVE CONSTRUCTION; FUNCTIONALIZED PYRROLIDINES; STEREOSPECIFIC SYNTHESIS; NITROGEN-HETEROCYCLES; ASYMMETRIC-SYNTHESIS; AZOMETHINE IMINES; ANNULATION;

D O I：

10.1002/ajoc.202100296

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An Iridium-catalyzed [4+3] cyclization of ortho-tosylaminophenyl-substituted para-quinone methides with vinylic oxiranes or vinyl aziridines has been successfully developed. In the presence of [Ir(cod)Cl](2) and a suitable base, this unprecedented cascade reaction occurs readily in good yield (up to 97%) and high diastereoselectivity (dr>20 : 1), providing a highly efficient synthetic approach to synthetically valuable seven-membered heterocyclic frameworks.

引用

页码：2152 / 2156

页数：5

共 30 条

[1] Metal-Catalyzed (4+3) Cyclization of Vinyl Aziridines with para-Quinone Methide Derivatives
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