Electron-Deficient Alkynes as Dipolarophile in Pd-Catalyzed Enantioselective (3+2) Cycloaddition Reaction with Vinyl Cyclopropanes

被引：49

作者：

Ding, Wen-Ping ^{[1
,2
,3
]}

Zhang, Gao-Peng ^{[1
]}

Jiang, Yang-Jie ^{[1
]}

Du, Juan ^{[1
]}

Liu, Xiu-Yan ^{[1
]}

Chen, Di ^{[1
]}

Ding, Chang-Hua ^{[1
,4
]}

Deng, Qing-Hai ^{[2
,3
]}

Hou, Xue-Long ^{[1
,5
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, Ctr Excellence Mol Synth, State Key Lab Organometall Chem, 345 Lingling Rd, Shanghai 200032, Peoples R China

[2] Shanghai Normal Univ, Educ Minist, Key Lab Resource Chem, Shanghai 200234, Peoples R China

[3] Shanghai Normal Univ, Shanghai Key Lab Rare Earth Funct Mat, Shanghai 200234, Peoples R China

[4] Shanghai Univ, Innovat Drug Res Ctr, Dept Chem, Shanghai 200444, Peoples R China

[5] Chinese Acad Sci, Shanghai Inst Organ Chem, Shanghai Hong Kong Joint Lab Chem Synth, 345 Lingling Rd, Shanghai 200032, Peoples R China

来源：

ORGANIC LETTERS | 2019年 / 21卷 / 17期

基金：

中国国家自然科学基金;

关键词：

DECARBOXYLATIVE CYCLOADDITION; DEAROMATIVE CYCLOADDITION; VINYLETHYLENE CARBONATES; ACTIVATED OLEFINS; FACILE SYNTHESIS; AZIRIDINES; CONSTRUCTION; VINYLCYCLOPROPANES; EPOXIDES; IMINES;

D O I：

10.1021/acs.orglett.9b02431

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The activated alkynes have been used successfully for the first time as the dipolarophile in the palladium-catalyzed asymmetric (3 + 2) cycloaddition, affording highly functionalized cyclopentenes in good to high yields with high chemoselectivities and good to high enantioselectivities. The introduction of an additional carbonyl group at the alpha-position of the alkynyl esters is the key to activating the carbon-carbon triple bond. The reaction process was investigated, and an inverse process of Pd-catalyzed (3 + 2) cycloaddition was observed.

引用

页码：6805 / 6810

页数：6

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