Recent advances in the enantioselective 1,3-dipolar cycloaddition of azomethine ylides and dipolarophiles

被引：122
作者：
Bdiri, Bilel [1 ]
Zhao, Boa-Jing [1 ]
Zhou, Zhi-Ming [1 ,2 ]
机构：
[1] Beijing Inst Technol, Sch Chem Engn & Environm, R&D Ctr Pharmaceut, 5th Zhongguancun South St, Beijing 100081, Peoples R China
[2] Beijing Inst Technol, State Key Lab Explos Sci & Technol, 5th Zhongguancun South St, Beijing 100081, Peoples R China
来源：
TETRAHEDRON-ASYMMETRY | 2017年 / 28卷 / 07期
关键词：
ASYMMETRIC 3+2 CYCLOADDITION; NON-BIARYL ATROPISOMERS; IMINO ESTERS; STEREOSELECTIVE-SYNTHESIS; CATALYZED CYCLOADDITION; CONJUGATE ADDITION; MICHAEL ADDITION; SPIRO-QUATERNARY; CONSTRUCTION; DERIVATIVES;
D O I：
10.1016/j.tetasy.2017.05.010
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
The synthesis of diastereo- and enantiopure heterocyclic molecules via catalytic asymmetric 1,3-dipolar cycloaddition reaction between azomethine ylides, generated in situ from alpha-amino acid-derived iminoesters and dipolarophiles is considered one of the most powerful and versatile techniques. In this review, we make a detailed overview of the latest developments in this area since 2014 and highlight the recent improvements in the structural scope of dipolarophiles, azomethine ylide precursors, and chiral ligands. (C) 2017 Elsevier Ltd. All rights reserved.
引用
收藏
页码：876 / 899
页数：24
相关论文
共 127 条
[1]   Recent advances in the catalytic asymmetric 1,3-dipolar cycloaddition of azomethine ylides [J].
Adrio, Javier ;
Carretero, Juan C. .
CHEMICAL COMMUNICATIONS, 2014, 50 (83) :12434-12446
[2]   Novel dipolarophiles and dipoles in the metal-catalyzed enantioselective 1,3-dipolar cycloaddition of azomethine ylides [J].
Adrio, Javier ;
Carretero, Juan C. .
CHEMICAL COMMUNICATIONS, 2011, 47 (24) :6784-6794
[3]   CHIRAL CO(II) AND MN(II) CATALYSTS FOR THE 1,3-DIPOLAR CYCLOADDITION REACTIONS OF AZOMETHINE YLIDES DERIVED FROM ARYLIDENE IMINES OF GLYCINE [J].
ALLWAY, P ;
GRIGG, R .
TETRAHEDRON LETTERS, 1991, 32 (41) :5817-5820
[4]   A Novel One-Pot Green Synthesis of Dispirooxindolo-pyrrolidines via 1,3-Dipolar Cycloaddition Reactions of Azomethine Ylides [J].
Almansour, Abdulrahman I. ;
Arumugam, Natarajan ;
Kumar, Raju Suresh ;
Periyasami, Govindasami ;
Ghabbour, Hazem A. ;
Fun, Hoong-Kun .
MOLECULES, 2015, 20 (01) :780-791
[5]   Enantioselective synthesis of the spirotryprostatin A scaffold [J].
Antonchick, Andrey P. ;
Schuster, Hannah ;
Bruss, Hanna ;
Schuermann, Markus ;
Preut, Hans ;
Rauh, Daniel ;
Waldmann, Herbert .
TETRAHEDRON, 2011, 67 (52) :10195-10202
[6]   Highly enantioselective synthesis and cellular evaluation of spirooxindoles inspired by natural products [J].
Antonchick, Andrey P. ;
Gerding-Reimers, Claas ;
Catarinella, Mario ;
Schuermann, Markus ;
Preut, Hans ;
Ziegler, Slava ;
Rauh, Daniel ;
Waldmann, Herbert .
NATURE CHEMISTRY, 2010, 2 (09) :735-740
[7]   PyBidine-Cu(OTf)2-Catalyzed Asymmetric [3+2] Cycloaddition with Imino Esters: Harmony of Cu-Lewis Acid and Imidazolidine-NH Hydrogen Bonding in Concerto Catalysis [J].
Arai, Takayoshi ;
Ogawa, Hiroki ;
Awata, Atsuko ;
Sato, Makoto ;
Watabe, Megumi ;
Yamanaka, Masahiro .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (05) :1595-1599
[8]   Chiral Bis(imidazolidine)pyridine-Cu(OTf)2: Catalytic Asymmetric Endo-Selective [3+2] Cycloaddition of Imino Esters with Nitroalkenes [J].
Arai, Takayoshi ;
Mishiro, Asami ;
Yokoyama, Naota ;
Suzuki, Kuniko ;
Sato, Hiroyasu .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (15) :5338-+
[9]   Catalytic Asymmetric Synthesis of Bicycloprolines by a 1,3-Dipolar Cycloaddition/Intramolecular Alkylation Strategy [J].
Arpa, Enrique M. ;
Gonzalez-Esguevillas, Maria ;
Pascual-Escudero, Ana ;
Adrio, Javier ;
Carretero, Juan C. .
JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (14) :6128-6135
[10]   PyBidine/Copper Catalyst: Asymmetric exo′-Selective [3+2] Cycloaddition using Imino Ester and Electrophilic Indole [J].
Awata, Atsuko ;
Arai, Takayoshi .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (39) :10462-10465
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