Recent advances in the catalytic asymmetric 1,3-dipolar cycloaddition of azomethine ylides

被引:335
作者
Adrio, Javier [1 ]
Carretero, Juan C. [1 ]
机构
[1] Univ Autonoma Madrid, Fac Ciencias, Dept Quim Organ, E-28049 Madrid, Spain
关键词
ENANTIOSELECTIVE 3+2 CYCLOADDITION; DIELS-ALDER REACTIONS; X=Y-ZH COMPOUNDS; ONE-POT; PYRROLIDINE DERIVATIVES; EFFICIENT CONSTRUCTION; POTENTIAL 1,3-DIPOLES; CHIRAL CATALYSTS; FACILE ACCESS; AMINO ESTERS;
D O I
10.1039/c4cc04381b
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Catalytic asymmetric 1,3-dipolar cycloadditions of azomethine ylides have turned out to be one of the most efficient methods for the preparation of enantioenriched pyrrolidines. The past decade has witnessed the development of a bunch of well-defined catalytic systems capable of affording excellent diastereo and enantioselectivities. Recently, a great effort has been focused on expanding the scope of the cycloaddition with regard to both reaction partners. In this review, we will discuss important advances that have been reported in this area since 2011.
引用
收藏
页码:12434 / 12446
页数:13
相关论文
共 127 条
[1]   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
[2]   A convenient procedure for the catalytic asymmetric 1,3-dipolar cycloaddition of azomethine ylides and alkenes [J].
Alemparte, C ;
Blay, G ;
Jorgensen, KA .
ORGANIC LETTERS, 2005, 7 (21) :4569-4572
[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]   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
[5]   Catalytic Asymmetric exo'-Selective [3+2] Cycloaddition of Iminoesters with Nitroalkenes [J].
Arai, Takayoshi ;
Yokoyama, Naota ;
Mishiro, Asami ;
Sato, Hiroyasu .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (43) :7895-7898
[6]   Catalytic Asymmetric exo'-Selective [3+2] Cycloaddition for Constructing Stereochemically Diversified Spiro[pyrrolidin-3,3'-oxindole]s [J].
Awata, Atsuko ;
Arai, Takayoshi .
CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (27) :8278-8282
[7]   Metal-Free Asymmetric 1,3-Dipolar Cycloaddition of N-Arylmaleimides to Azomethine Ylides Catalyzed by Chiral Tertiary Amine Thiourea [J].
Bai, Jian-Fei ;
Wang, Liang-Liang ;
Peng, Lin ;
Guo, Yun-Long ;
Ming, Jun-Nan ;
Wang, Fei-Ying ;
Xu, Xiao-Ying ;
Wang, Li-Xin .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (23) :4472-4478
[8]   Asymmetric 1,3-dipolar cycloadditions of cyclic stabilized ylides derived from chiral 1,2-amino alcohols [J].
Bonin, Martine ;
Chauveau, Ariane ;
Micouin, L. .
SYNLETT, 2006, (15) :2349-2363
[9]   Highly enantioselective copper(I)-fesulphos-catalyzed 1,3-dipolar cycloaddition of azomethine ylides [J].
Cabrera, S ;
Arrayás, RG ;
Carretero, JC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (47) :16394-16395
[10]   Phosphoramidite-Cu(OTf)2 Complexes as Chiral Catalysts for 1,3-Dipolar Cycloaddition of lminoesters and Nitroalkenes [J].
Castello, Luis M. ;
Najera, Carmen ;
Sansano, Jose M. ;
Larranaga, Olatz ;
de Cozar, Abel ;
Cossio, Fernando P. .
ORGANIC LETTERS, 2013, 15 (12) :2902-2905