Novel bifunctional chiral squaramide-amine catalysts for highly enantioselective addition of mono- and diketones to nitroalkenes

被引：25

作者：

Dong, Ze ^{[1
]}

Jin, Xiaoqing ^{[1
]}

Wang, Pengcheng ^{[1
]}

Min, Chang ^{[1
]}

Zhang, Jin ^{[1
]}

Chen, Zhe ^{[1
]}

Zhou, Hai-Bing ^{[1
,2
]}

Dong, Chune ^{[1
,2
]}

机构：

[1] Wuhan Univ, Coll Pharm, State Key Lab Virol, Wuhan 430071, Peoples R China

[2] Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Organofluorine Chem, Shanghai 200032, Peoples R China

来源：

ARKIVOC | 2011年

基金：

高等学校博士学科点专项科研基金;

关键词：

Chiral squaramide-amine; organocatalyst; asymmetric Michael addition; pyrrolidine; cinchonine; ASYMMETRIC MICHAEL ADDITION; SQUARIC ACID; ALPHA; ALPHA-DISUBSTITUTED ALDEHYDES; 1,3-DICARBONYL COMPOUNDS; PYRROLIDINE-THIOUREA; CONJUGATE ADDITION; KETONES; DERIVATIVES; EFFICIENT; REDUCTION;

D O I：

10.3998/ark.5550190.0012.927

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Novel bifunctional chiral squaramide-amine organocatalysts have been developed by rational combination of pyrrolidine and a cinchona alkaloid. The catalysts promoted the enantioselective Michael addition of both mono- and diketones to a broad range of nitroalkenes providing the corresponding products in moderate to high yields with excellent enantioselectivities and diastereoselectivities (up to 96% yield, 96% ee, 98: 2 dr) under mild conditions. These results demonstrate that the assembly of two chiral privileged skeletons, pyrrolidine and cinchonine with a squaramide linker is a useful strategy to reach a wider substrate scope, high reaction efficiency and enantioselectivity. The match of the chiralities between two backbones embedded in the catalysts is also critical for improving enantioselectivity.

引用

页码：367 / +

页数：61

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