Chiral multifunctional thiourea-phosphine catalyzed asymmetric [3+2] annulation of Morita-Baylis-Hillman carbonates with maleimides

被引：32

作者：

Deng, Hong-Ping ^{[1
]}

Wang, De ^{[2
,3
]}

Wei, Yin ^{[1
]}

Shi, Min ^{[1
,2
,3
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China

[2] E China Univ Sci & Technol, Sch Chem & Mol Engn, Key Lab Adv Mat, Shanghai 200237, Peoples R China

[3] E China Univ Sci & Technol, Sch Chem & Mol Engn, Inst Fine Chem, Shanghai 200237, Peoples R China

来源：

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 8卷

基金：

中国国家自然科学基金;

关键词：

asymmetric [3+2] annulation; maleimides; Morita-Baylis-Hillman carbonates; multifunctional thiourea-phosphine; organocatalysis; ELECTRON-DEFICIENT OLEFINS; MODIFIED ALLYLIC COMPOUNDS; FUNCTIONALIZED CYCLOPENTENES; CYCLOADDITION; IMINES; 2,3-BUTADIENOATES; ORGANOCATALYSTS; CONSTRUCTION; CYCLIZATION; ALLENOATES;

D O I：

10.3762/bjoc.8.121

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We have developed a multifunctional thiourea-phosphine catalyzed asymmetric [3 + 2] annulation of Morita-Baylis-Hillman (MBH) carbonates with maleimides, which can efficiently construct functionalized cyclopentenes bearing three contiguous stereocenters in moderate to excellent yields and excellent diastereo- and enantioselectivities. A plausible mechanism has been also proposed on the basis of control experiments and previous literature.

引用

页码：1098 / 1104

页数：7

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