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.

引用

页码：2677 / 2682

页数：6

共 48 条

[31] Direct asymmetric Mannich reaction of phthalides: facile access to chiral substituted isoquinolines and isoquinolinones [J].

Luo, Jie ;

Wang, Haifei ;

Zhong, Fangrui ;

Kwiatkowski, Jacek ;

Xu, Li-Wen ;

Lu, Yixin .

CHEMICAL COMMUNICATIONS, 2012, 48 (39) :4707-4709

[32] Organocatalytic highly enantioselective nitroaldol reaction of α-ketophosphonates and nitromethane [J].

Mandal, Tanmay ;

Samanta, Sampak ;

Zhao, Cong-Gui .

ORGANIC LETTERS, 2007, 9 (05) :943-945

[33] Cobalt-Bisoxazoline-Catalyzed Asymmetric Kumada Cross-Coupling of Racemic α-Bromo Esters with Aryl Grignard Reagents [J].

Mao, Jianyou ;

Liu, Feipeng ;

Wang, Min ;

Wu, Lin ;

Zheng, Bing ;

Liu, Shangzhong ;

Zhong, Jiangchun ;

Bian, Qinghua ;

Walsh, Patrick J. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (50) :17662-17668

[34] Design, Synthesis, and Structural Analysis of Phenylpropanoic Acid-Type PPARγ-Selective Agonists Discovery of Reversed Stereochemistry-Activity Relationship [J].

Ohashi, Masao ;

Oyama, Takuji ;

Nakagome, Izumi ;

Satoh, Mayumi ;

Nishio, Yoshino ;

Nobusada, Hiromi ;

Hirono, Shuichi ;

Morikawa, Kosuke ;

Hashimoto, Yuichi ;

Miyachi, Hiroyuki .

JOURNAL OF MEDICINAL CHEMISTRY, 2011, 54 (01) :331-341

[35] Organocatalytic Highly Enantioselective Synthesis of β-Formyl-α-hydroxyphosphonates [J].

Perera, Sandun ;

Naganaboina, Vijaya Kumar ;

Wang, Long ;

Zhang, Bin ;

Guo, Qunsheng ;

Rout, Laxmidhar ;

Zhao, Cong-Gui .

ADVANCED SYNTHESIS & CATALYSIS, 2011, 353 (10) :1729-1734

[36] Organocatalytic enantioselective synthesis of α-hydroxy phosphonates [J].

Samanta, Sampak ;

Zhao, Cong-Gui .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (23) :7442-7443

[37] Enantioselective Conjugate Addition of Both Aromatic Ketones and Acetone to Nitroolefins Catalyzed by Chiral Primary Amines Bearing Multiple Hydrogen-Bonding Donors [J].

Sun, Zhong-Wen ;

Peng, Fang-Zhi ;

Li, Ze-Qian ;

Zou, Li-Wei ;

Zhang, Shao-Xiong ;

Li, Xiang ;

Shao, Zhi-Hui .

JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (08) :4103-4110

[38] Asymmetric conjugate addition of silyl enol ethers catalyzed by tethered bis(8-quinolinolato) aluminum complexes [J].

Takenaka, Norito ;

Abell, Joshua P. ;

Yamamoto, Hisashi .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (04) :742-743

[39] Rationally Designed Amide Donors for Organocatalytic Asymmetric Michael Reactions [J].

Tan, Bin ;

Hernandez-Torres, Gloria ;

Barbas, Carlos F., III .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (22) :5381-5385

[40] Asymmetric Phase-Transfer Catalysts Bearing Multiple Hydrogen-Bonding Donors: Highly Efficient Catalysts for Enantio- and Diastereoselective Nitro-Mannich Reaction of Amidosulfones [J].

Wang, Bin ;

Liu, Yuxin ;

Sun, Cong ;

Wei, Zhonglin ;

Cao, Jungang ;

Liang, Dapeng ;

Lin, Yingjie ;

Duan, Haifeng .

ORGANIC LETTERS, 2014, 16 (24) :6432-6435

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