Asymmetric Conjugate Addition of 1,3-Diketone to Nitroalkenes Catalyzed by Bifunctional Thiourea-Amide Organocatalysts

doi:10.6023/cjoc201809015

Chin. J. Org. Chem. ›› 2019, Vol. 39 ›› Issue (4): 1053-1063.DOI: 10.6023/cjoc201809015 Previous Articles Next Articles

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手性硫脲-酰胺催化1,3-二酮对硝基烯烃的不对称Michael加成反应

白冰^a, 王龙^a, 杨静^a, 蔡莉莉^b, 刘前进^b, 席高磊^b, 赵志伟^b, 毛多斌^a, 陈芝飞^b

a 郑州轻工业学院食品与生物工程学院郑州 450000;
b 河南中烟工业有限责任公司技术中心郑州 450000

收稿日期:2018-09-10 修回日期:2018-11-14 发布日期:2018-12-28
通讯作者: 毛多斌, 陈芝飞 E-mail:maoduobin@sohu.com;chenzhifei@126.com
基金资助:
河南省科技厅（No.172102210068）、郑州轻工业学院（No.2013BSJJ009）资助项目.

Asymmetric Conjugate Addition of 1,3-Diketone to Nitroalkenes Catalyzed by Bifunctional Thiourea-Amide Organocatalysts

Bai Bing^a, Wang Long^a, Yang Jing^a, Cai Lili^b, Liu Qianjin^b, Xi Gaolei^b, Zhao Zhiwei^b, Mao Duobin^a, Chen Zhifei^b

a School of Food & Biological Engineering, Zhengzhou University of Light Industry, Zhengzhou 450000;
b Technology Center, China Tobacco Henan Industrial Co., Ltd., Zhengzhou 450000

Received:2018-09-10 Revised:2018-11-14 Published:2018-12-28
Contact: 10.6023/cjoc201809015 E-mail:maoduobin@sohu.com;chenzhifei@126.com
Supported by:
Project supported by the Department of Science and Technology of Henan Province (No.172102210068) and the Zhengzhou University of Light Industry (No.2013BSJJ009).

1. Asymmetric Conjugate Addition of 1,3-Diketone to Nitroalkenes Catalyzed by Bifunctional Thiourea-Amide Organocatalysts.PDF(5886KB)

Abstract

New bifunctional chiral thiourea-amide organocatalysts were developed. Their applications in asymmetric conjugate addition of 2,4-pentandione to various nitroalkenes were investigated. The corresponding adducts were obtained in excellent yields with high enantioselectivities up to 94% ee in present of 1 mol% catalyst. The catalytic system could also suit for various nitroalkenes bearing electron-donating or electron-withdrawing groups. The preliminary structure-activity relationship study reveals that the acyl group in pyrrolidine N position plays an important role in catalyzing the reaction.

Key words: thiourea-amide, organocatalyst, Michael addition, asymmetric

Cite this article

Bai Bing, Wang Long, Yang Jing, Cai Lili, Liu Qianjin, Xi Gaolei, Zhao Zhiwei, Mao Duobin, Chen Zhifei. Asymmetric Conjugate Addition of 1,3-Diketone to Nitroalkenes Catalyzed by Bifunctional Thiourea-Amide Organocatalysts[J]. Chin. J. Org. Chem., 2019, 39(4): 1053-1063.

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手性硫脲-酰胺催化1,3-二酮对硝基烯烃的不对称Michael加成反应

Asymmetric Conjugate Addition of 1,3-Diketone to Nitroalkenes Catalyzed by Bifunctional Thiourea-Amide Organocatalysts

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