Literature DB >> 29560980

Catalytic asymmetric construction of spiropyrrolidines via 1,3-dipolar cycloaddition of azomethine ylides.

Xin Fang1, Chun-Jiang Wang2.   

Abstract

Spirocyclic pyrrolidines are structural motifs frequently found in a wide variety of natural products, pharmaceuticals and biologically significant compounds. In the past few years, catalytic asymmetric 1,3-dipolar cycloaddition reactions of azomethine ylides have shown to be one of the most straightforward methods for the stereoselective preparation of diverse biologically important spiropyrrolidine heterocycles in high yields with excellent enantioselectivities under mild reaction conditions. In this review, we will discuss the recent major developments in the catalytic enantioselective synthesis of chiral spiropyrrolidine derivatives since 2009.

Entities:  

Year:  2018        PMID: 29560980     DOI: 10.1039/C7OB02686B

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN: 1477-0520            Impact factor:   3.876


  13 in total

1.  Synthesis of DNA-coupled isoquinolones and pyrrolidines by solid phase ytterbium- and silver-mediated imine chemistry.

Authors:  Marco Potowski; Verena B K Kunig; Florian Losch; Andreas Brunschweiger
Journal:  Medchemcomm       Date:  2019-02-26       Impact factor: 3.597

2.  Three-Component [3+2] Cycloaddition for Regio- and Diastereoselective Synthesis of Spirooxindole-Pyrrolidines.

Authors:  Xiaofeng Zhang; Miao Liu; Desheng Zhan; Manpreet Kaur; Jerry P Jasinski; Wei Zhang
Journal:  New J Chem       Date:  2022-01-20       Impact factor: 3.925

3.  Regio- and stereoselective synthesis of spiropyrrolidine-oxindole and bis-spiropyrrolizidine-oxindole grafted macrocycles through [3 + 2] cycloaddition of azomethine ylides.

Authors:  Perumal Prabhakaran; Perumal Rajakumar
Journal:  RSC Adv       Date:  2020-03-10       Impact factor: 4.036

4.  Predicting Absolute Rate Constants for Huisgen Reactions of Unsaturated Iminium Ions with Diazoalkanes.

Authors:  Jingjing Zhang; Quan Chen; Robert J Mayer; Jin-Dong Yang; Armin R Ofial; Jin-Pei Cheng; Herbert Mayr
Journal:  Angew Chem Int Ed Engl       Date:  2020-05-11       Impact factor: 15.336

5.  Stereodivergent assembly of tetrahydro-γ-carbolines via synergistic catalytic asymmetric cascade reaction.

Authors:  Shi-Ming Xu; Liang Wei; Chong Shen; Lu Xiao; Hai-Yan Tao; Chun-Jiang Wang
Journal:  Nat Commun       Date:  2019-12-05       Impact factor: 14.919

Review 6.  Transition metal-catalyzed synthesis of spirooxindoles.

Authors:  P V Saranya; Mohan Neetha; Thaipparambil Aneeja; Gopinathan Anilkumar
Journal:  RSC Adv       Date:  2021-02-10       Impact factor: 3.361

7.  Redox-neutral manganese-catalyzed synthesis of 1-pyrrolines.

Authors:  Tingting Feng; Canxiang Liu; Zhen Wu; Xinxin Wu; Chen Zhu
Journal:  Chem Sci       Date:  2022-02-09       Impact factor: 9.825

8.  Catalytic asymmetric synthesis of enantioenriched α-deuterated pyrrolidine derivatives.

Authors:  Xin Chang; Xiang Cheng; Chun-Jiang Wang
Journal:  Chem Sci       Date:  2022-03-17       Impact factor: 9.825

9.  Catalytic asymmetric synthesis of 3,2'-pyrrolinyl spirooxindoles via conjugate addition/Schmidt-type rearrangement of vinyl azides and (E)-alkenyloxindoles.

Authors:  Ziwei Zhong; Zhijie Xiao; Xiaohua Liu; Weidi Cao; Xiaoming Feng
Journal:  Chem Sci       Date:  2020-09-28       Impact factor: 9.825

10.  Catalytic Asymmetric Formal [3+2] Cycloaddition of Azoalkenes with 3-Vinylindoles: Synthesis of 2,3-Dihydropyrroles.

Authors:  Guang-Jian Mei; Wenrui Zheng; Théo P Gonçalves; Xiwen Tang; Kuo-Wei Huang; Yixin Lu
Journal:  iScience       Date:  2020-01-31
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