Cu(i)-Catalyzed asymmetric exo-selective synthesis of substituted pyrrolidines via a 1,3-dipolar cycloaddition reaction

被引:8
作者
Biswas, Rayhan G. [1 ]
Ray, Sumit K. [2 ]
Kannaujiya, Vinod K. [1 ]
Unhale, Rajshekhar A. [1 ]
Singh, Vinod K. [3 ]
机构
[1] Indian Inst Sci Educ & Res Bhopal, Dept Chem, Bhopal 462066, Madhya Pradesh, India
[2] Kharagpur Coll, Dept Chem, Paschim Medinipur 721305, W Bengal, India
[3] Indian Inst Technol Kanpur, Dept Chem, Kanpur 208016, Uttar Pradesh, India
关键词
ENANTIOSELECTIVE 3+2 CYCLOADDITION; AZOMETHINE YLIDES; CONSTRUCTION; DIASTEREO; DIPOLAROPHILES; DERIVATIVES; CATALYSTS; STEREOSELECTIVITY; COMPLEXES; FRAMEWORK;
D O I
10.1039/d1ob00494h
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An (R)-DM-BINAP/Cu(CH3CN)(4)BF4 complex catalyzed exo-selective asymmetric 1,3-dipolar cycloaddition (1,3-DCA) reaction of imino esters with alpha,beta-unsaturated pyrazoleamides has been developed. A series of highly functionalized pyrrolidines with multiple stereogenic centers were obtained with good yields and diastereoselectivities and excellent enantioselectivities (up to 99% ee).
引用
收藏
页码:4685 / 4690
页数:6
相关论文
共 86 条
[1]   Stereochemical diversity in pyrrolidine synthesis by catalytic asymmetric 1,3-dipolar cycloaddition of azomethine ylides [J].
Adrio, Javier ;
Carretero, Juan C. .
CHEMICAL COMMUNICATIONS, 2019, 55 (80) :11979-11991
[2]   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
[3]   Total Synthesis of L-(+)-Swainsonine and Other Indolizidine Azasugars from D-Glucose [J].
Alam, Mohammad Abrar ;
Kumar, Amit ;
Vankar, Yashwant D. .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 2008 (29) :4972-4980
[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 for Constructing Stereochemically Diversified Spiro[pyrrolidin-3,3'-oxindole]s [J].
Awata, Atsuko ;
Arai, Takayoshi .
CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (27) :8278-8282
[6]   N-tert-Butanesulfinyl imine and aromatic tertiary amide derived non-biaryl atropisomers as chiral ligands for silver-catalyzed endo-selective [3+2] cycloaddition of azomethine ylides with maleimides [J].
Bai, Xing-Feng ;
Zhang, Jin ;
Xia, Chun-Gu ;
Xu, Jian-Xing ;
Xu, Li-Wen .
TETRAHEDRON, 2016, 72 (21) :2690-2699
[7]   Recent advances in the enantioselective 1,3-dipolar cycloaddition of azomethine ylides and dipolarophiles [J].
Bdiri, Bilel ;
Zhao, Boa-Jing ;
Zhou, Zhi-Ming .
TETRAHEDRON-ASYMMETRY, 2017, 28 (07) :876-899
[8]   CuII-catalysed asymmetric 1,3-dipolar cycloaddition of azomethine ylides with a chiral ferrocene-derived P,N-ligand [J].
Bdiri, Bilel ;
Dai, Li ;
Zhou, Zhi-Ming .
TETRAHEDRON LETTERS, 2017, 58 (25) :2475-2481
[9]   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
[10]   Catalytic asymmetric [3+2] cycloaddition of azomethine ylides. Development of a versatile stepwise, three-component reaction for diversity-oriented synthesis [J].
Chen, C ;
Li, XD ;
Schreiber, SL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (34) :10174-10175