Convergent Synthesis of Dihydropyrans from Catalytic Three-Component Reactions of Vinylcyclopropanes, Diazoesters, and Diphenyl Sulfoxide

被引：9

作者：

Zhang, Ya-Lin ^{[1
,2
]}

Guo, Rui-Ting ^{[1
,2
]}

Luo, Heng ^{[1
,2
]}

Liang, Xin-Shen ^{[1
,2
]}

Wang, Xiao-Chen ^{[1
,2
]}

机构：

[1] Nankai Univ, Coll Chem, State Key Lab, Tianjin 300071, Peoples R China

[2] Nankai Univ, Coll Chem, Inst Elementoorgan Chem, Tianjin 300071, Peoples R China

来源：

ORGANIC LETTERS | 2020年 / 22卷 / 14期

基金：

中国国家自然科学基金;

关键词：

C-C BOND; INTRAMOLECULAR 3+2 CYCLOADDITION; ENE-VINYLCYCLOPROPANES; INTERMOLECULAR 5+2; METAL; CARBON; 1ST; ISOMERIZATION; INSERTION; ALLENES;

D O I：

10.1021/acs.orglett.0c01992

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel Rh(I)/La(III) cocatalytic three-component reaction of vinylcyclopropanes, diazoesters, and diphenyl sulfoxide has been developed. The reaction gives polysubstituted dihydropyrans as the reaction products. Mechanistic studies indicate that isomerization of vinylcyclopropanes gives conjugated dienes, which then undergo [4 + 2]-cycloaddition with vicinal tricarbonyl compounds generated by oxygen atom transfer from diphenyl sulfoxide to diazoesters.

引用

页码：5627 / 5632

页数：6

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