Modular Synthesis of Azidobicyclo[2.1.1]hexanes via (3+2) Annulation of α-Substituted Vinyl Azides and Bicyclo[1.1.0]butanes

被引：10

作者：

Hu, Sai ^{[1
,2
]}

Gao, Yuhong ^{[1
,2
]}

Pan, Yuming ^{[1
]}

Ni, Dongshun ^{[1
,2
]}

Deng, Li ^{[1
,2
]}

机构：

[1] Westlake Univ, Sch Sci, Dept Chem, Key Lab Precise Synth Funct Mol Zhejiang Prov, Hangzhou 310030, Zhejiang, Peoples R China

[2] Westlake Univ, Res Ctr Ind Future, Hangzhou 310030, Zhejiang, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 89卷 / 20期

基金：

中国国家自然科学基金;

关键词：

DONOR-ACCEPTOR CYCLOPROPANES; 2-PI+2-SIGMA CYCLOADDITIONS; PYRIDINE; RELEASE; DESIGN;

D O I：

10.1021/acs.joc.4c01920

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Here, we present a mild and rapid method to access azidobicyclo[2.1.1]hexanes via formal (3 + 2) cycloaddition of alpha-substituted vinyl azides and bicyclo[1.1.0]butanes under Lewis acid catalysis. A wide range of alpha-substituted vinyl azides were tolerated under mild conditions. Notably, the resulting cycloadducts could be transformed into structurally attractive 3-azabicyclo[3.1.1]heptenes through microwave-promoted rearrangement. The utilities were highlighted by copper(I)-catalyzed Huisgen 1,3-dipolar cycloaddition of tertiary alkyl azide and further transformation of the azide and ketone groups.

引用

页码：15151 / 15157

页数：7

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