Highly enantioselective organocatalytic Biginelli reaction

被引:305
作者
Chen, Xiao-Hua
Xu, Xiao-Ying
Liu, Hua
Cun, Lin-Feng
Gong, Liu-Zhu [1 ]
机构
[1] Chinese Acad Sci, Chengdu Inst Organ Chem, Chengdu 610041, Peoples R China
[2] Univ Sci & Technol China, Hefei Natl Lab Phys Sci Microscale, Hefei 230026, Peoples R China
[3] Univ Sci & Technol China, Dept Chem, Hefei 230026, Peoples R China
[4] Chinese Acad Sci, Grad Sch, Beijing, Peoples R China
关键词
D O I
10.1021/ja065267y
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A series of binol- and H8-binol-based phosphoric acids have for the first time been evaluated for their ability to catalyze Biginelli reactions of aldehydes, thiourea or urea, and β-keto esters. A new chiral phosphoric acid, derived from 3,3′-diphenyl-H8-binol, exhibited superior catalytic activity and enantioselectivity compared to its structural analogues, affording high enantioselectivities ranging from 85 to 97% ee with a wide scope of substrates. A metal-free preparation of optically active monastrol was achieved on the basis of the current process. Copyright © 2006 American Chemical Society.
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收藏
页码:14802 / 14803
页数:2
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