Asymmetric Construction of Pyrrolidines Bearing a Trifluoromethylated Quaternary Stereogenic Center via CuI-Catalyzed 1,3-Dipolar Cycloaddition of Azomethine Ylides with -CF3-,-Disubstituted Nitroalkenes

被引：24

作者：

Tang, Li-Wei ^{[1
]}

Zhao, Bao-Jing ^{[1
]}

Dai, Li ^{[1
]}

Zhang, Man ^{[1
]}

Zhou, Zhi-Ming ^{[1
,2
]}

机构：

[1] Beijing Inst Technol, R&D Ctr Pharmaceut, Sch Chem Engn & Environm, 5th Zhongguancun South St, Beijing, Peoples R China

[2] Beijing Inst Technol, State Key Lab Explos Sci & Technol, 5th Zhongguancun South St, Beijing, Peoples R China

来源：

CHEMISTRY-AN ASIAN JOURNAL | 2016年 / 11卷 / 17期

关键词：

copper; cycloaddition; ferrocenyloxazolinylphosphines; pyrrolidine; trifluoromethylation; ENANTIOSELECTIVE CONSTRUCTION; MEDICINAL CHEMISTRY; CARBON STEREOCENTERS; FLUORINE; REACTIVITY; DESIGN; BOND;

D O I：

10.1002/asia.201600941

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A direct and convenient method has been developed for the synthesis of optically active pyrrolidines bearing a quaternary stereogenic center containing a CF3 group at the C-3 position of the pyrrolidine ring. The synthesis system, Cu-I/Si-FOXAP-catalyzed exo-selective 1,3-dipolar cycloaddition of azomethine ylides with -CF3-,-disubstituted nitroalkenes, provides pyrrolidines with high diastereoselectivities (up to >98:2 d.r.) and excellent enantioselectivities (up to >99.9 ee) and performs well for a broad scope of substrates under mild conditions.

引用

页码：2470 / 2477

页数：8

共 65 条

[11] Stereoselective construction of quaternary stereocenters [J].

Christoffers, J ;

Baro, A .

ADVANCED SYNTHESIS & CATALYSIS, 2005, 347 (11-13) :1473-1482

[12]

Christoffers J, 2001, ANGEW CHEM INT EDIT, V40, P4591, DOI 10.1002/1521-3773(20011217)40:24<4591::AID-ANIE4591>3.0.CO

[13]

2-V

[14]

Christoffers J., 2001, Angew. Chem, V113, P4725, DOI DOI 10.1002/1521-3757(20011217)113:24

[15]

Corey EJ, 1998, ANGEW CHEM INT EDIT, V37, P388, DOI 10.1002/(SICI)1521-3773(19980302)37:4<388::AID-ANIE388>3.0.CO

[16]

2-V

[17] The design, synthesis and application of imidazolium-tagged ferrocenyl oxazoline phosphine ligands for the asymmetric 1,3-dipolar cycloaddition of azomethine ylides with nitroalkenes: ion effect for enhancing the reactivity, stereoselectivity and recyclability [J].

Dai, Li ;

Xu, Di ;

Dong, Xiao ;

Zhou, Zhiming .

TETRAHEDRON-ASYMMETRY, 2015, 26 (07) :350-360

[18] A CuII-N,P Oxazolinylferrocene Ligand Complex for the Asymmetric [3+2] 1,3-Dipolar Cycloaddition of Azomethine Ylide with Malonates [J].

Dai, Li ;

Xu, Di ;

Tang, Li-Wei ;

Zhou, Zhi-Ming .

CHEMCATCHEM, 2015, 7 (07) :1078-1082

[19] Recent advances in organocatalytic methods for the synthesis of disubstituted 2-and 3-indolinones [J].

Dalpozzo, Renato ;

Bartoli, Giuseppe ;

Bencivenni, Giorgio .

CHEMICAL SOCIETY REVIEWS, 2012, 41 (21) :7247-7290

[20] Enantioselective synthesis of all-carbon quaternary stereogenic centers in acyclic systems [J].

Das, Jaya Prakash ;

Marek, Ilan .

CHEMICAL COMMUNICATIONS, 2011, 47 (16) :4593-4623

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