Organocatalytic Asymmetric Michael/Friedel-Crafts Cascade Reaction of 3-Pyrrolyl-oxindoles and α,β-Unsaturated Aldehydes for the Construction of Chiral Spiro[5,6-dihydropyrido[1,2-a]pyrrole-3,3′-oxindoles]

被引：49

作者：

You, Yong ^{[1
,3
]}

Cui, Bao-Dong ^{[2
]}

Zhou, Ming-Qiang ^{[1
,3
]}

Zuo, Jian ^{[1
,3
]}

Zhao, Jian-Qiang ^{[1
,3
]}

Xu, Xiao-Ying ^{[1
]}

Zhang, Xiao-Mei ^{[1
]}

Yuan, Wei-Cheng ^{[1
]}

机构：

[1] Chinese Acad Sci, Chengdu Inst Organ Chem, Natl Engn Res Ctr Chiral Drugs, Chengdu 610041, Peoples R China

[2] Zunyi Med Univ, Sch Pharm, Zunyi 563000, Peoples R China

[3] Univ Chinese Acad Sci, Beijing 10049, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2015年 / 80卷 / 11期

基金：

中国国家自然科学基金;

关键词：

NATURAL-PRODUCTS; DOMINO REACTIONS; ENANTIOSELECTIVE SYNTHESIS; 3-SUBSTITUTED OXINDOLES; HIGHLY EFFICIENT; SPIROOXINDOLES; NITROOLEFINS; STRATEGIES; ALKALOIDS; BEARING;

D O I：

10.1021/acs.joc.5b00597

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient and unprecedented organocatalytic asymmetric reaction of 3-pyrrolyl-oxindoles with alpha,beta-unsaturated aldehydes to generate spirocyclic oxindole compounds was developed. The reactions were catalyzed by diphenylprolinol silyl ether and 2-fluorobenzoic acid via an asymmetric Michael/Friedel-Crafts cascade process, followed by dehydration with p-toluenesulfonic acid to afford a wide variety of structurally diverse Spiro [5,6-dihydropyrido[1,2-a]pyrrole-3,3'-oxindole] derivatives in high yields (up to 93%) and with high to excellent diastereo- and enantioselectivities (up to >99:1 dr and 97% ee).

引用

页码：5951 / 5957

页数：7

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