Asymmetric Michael reaction of arylacetyl phosphonates to nitroalkenes with bifunctional amine-thiourea catalyst bearing multiple-hydrogen-bond donor: efficient construction of chiral α-substituted carboxylic ester compounds

被引：5

作者：

Zhang, Ming-Liang ^{[1
,2
]}

Chen, Lin ^{[1
,2
]}

You, Yong ^{[1
,2
]}

Wang, Zhen-Hua ^{[1
,2
]}

Yue, Deng-Feng ^{[1
,2
]}

Zhang, Xiao-Mei ^{[1
]}

Xu, Xiao-Ying ^{[1
]}

Yuan, Wei-Cheng ^{[1
]}

机构：

[1] Chinese Acad Sci, Chengdu Inst Organ Chem, Natl Engn Res Ctr Chiral Drugs, Chengdu 610041, Peoples R China

[2] Univ Chinese Acad Sci, Beijing 100049, Peoples R China

来源：

TETRAHEDRON | 2016年 / 72卷 / 21期

基金：

中国国家自然科学基金;

关键词：

Asymmetric catalysis; Organocatalysis; Michael reaction; Arylacetyl phosphonates; Nitroalkenes; ALPHA; BETA-UNSATURATED ACYL PHOSPHONATES; ENANTIOSELECTIVE SYNTHESIS; CONJUGATE ADDITION; QUATERNARY; OXINDOLES; IRIDIUM; COMPLEXES; DISCOVERY; LIGANDS; KETOPHOSPHONATES;

D O I：

10.1016/j.tet.2015.08.046

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Catalytic asymmetric Michael addition of arylacetyl phosphonates to nitroalkenes was achieved with a chiral bifunctional amine-thiourea bearing a multiple-hydrogen-bond donor as a catalyst. A range of alpha-substituted carboxylic ester compounds with contiguous tertiary stereocenters could be smoothly obtained in good yields (up to 85%) and with high to excellent diastereo- and enantioselectivities (up to >99:1 dr and 95% ee). The large scale experiment and facile synthesis of a chiral gamma-butyrolactam have also been demonstrated. (C) 2015 Elsevier Ltd. All rights reserved.

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页码：2677 / 2682

页数：6

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