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
收藏
页码：1098 / 1104
页数：7
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