Literature DB >> 31552927

Stereochemical diversity in pyrrolidine synthesis by catalytic asymmetric 1,3-dipolar cycloaddition of azomethine ylides.

Javier Adrio1, Juan C Carretero1.   

Abstract

The pyrrolidine ring is a privileged structural motif in synthetic and medicinal chemisty. This review aims to highlight the high versatility of the catalytic asymmetric 1,3-dipolar cycloaddition of azomethine ylides for access to different types of stereochemical patterns in enantioselective pyrrolidine synthesis. Special attention will be paid to stereodivergent procedures giving rise to different stereoisomers from the same starting materials.

Entities:  

Year:  2019        PMID: 31552927     DOI: 10.1039/c9cc05238k

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN: 1359-7345            Impact factor:   6.222


  10 in total

1.  Stereodivergent synthesis of enantioenriched azepino[3,4,5-cd]-indoles via cooperative Cu/Ir-catalyzed asymmetric allylic alkylation and intramolecular Friedel-Crafts reaction.

Authors:  Lu Xiao; Bo Li; Fan Xiao; Cong Fu; Liang Wei; Yanfeng Dang; Xiu-Qin Dong; Chun-Jiang Wang
Journal:  Chem Sci       Date:  2022-03-30       Impact factor: 9.969

2.  Enantioselective C-H Amination Catalyzed by Nickel Iminyl Complexes Supported by Anionic Bisoxazoline (BOX) Ligands.

Authors:  Yuyang Dong; Colton J Lund; Gerard J Porter; Ryan M Clarke; Shao-Liang Zheng; Thomas R Cundari; Theodore A Betley
Journal:  J Am Chem Soc       Date:  2021-01-04       Impact factor: 16.383

3.  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

Review 4.  The Huisgen Reaction: Milestones of the 1,3-Dipolar Cycloaddition.

Authors:  Martin Breugst; Hans-Ulrich Reissig
Journal:  Angew Chem Int Ed Engl       Date:  2020-05-25       Impact factor: 15.336

5.  Synthesis of bioactive fluoropyrrolidines via copper(i)-catalysed asymmetric 1,3-dipolar cycloaddition of azomethine ylides.

Authors:  Xiao Xu; Longzhu Bao; Lu Ran; Zhenyan Yang; Dingce Yan; Chun-Jiang Wang; Huailong Teng
Journal:  Chem Sci       Date:  2021-12-07       Impact factor: 9.825

6.  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

7.  Enantioselective 1,3-Dipolar Cycloaddition Using (Z)-α-Amidonitroalkenes as a Key Step to the Access to Chiral cis-3,4-Diaminopyrrolidines.

Authors:  Eduardo García-Mingüens; Marcos Ferrándiz-Saperas; M de Gracia Retamosa; Carmen Nájera; Miguel Yus; José M Sansano
Journal:  Molecules       Date:  2022-07-18       Impact factor: 4.927

8.  Zinc-Catalyzed Enantioselective [3+2] Cycloaddition of Azomethine Ylides Using Planar Chiral [2.2]Paracyclophane-Imidazoline N,O-ligands.

Authors:  Sundaravel Vivek Kumar; Patrick J Guiry
Journal:  Angew Chem Int Ed Engl       Date:  2022-06-09       Impact factor: 16.823

Review 9.  N-tert-Butanesulfinyl imines in the asymmetric synthesis of nitrogen-containing heterocycles.

Authors:  Joseane A Mendes; Paulo R R Costa; Miguel Yus; Francisco Foubelo; Camilla D Buarque
Journal:  Beilstein J Org Chem       Date:  2021-05-12       Impact factor: 2.883

Review 10.  Pyrrolidine in Drug Discovery: A Versatile Scaffold for Novel Biologically Active Compounds.

Authors:  Giovanna Li Petri; Maria Valeria Raimondi; Virginia Spanò; Ralph Holl; Paola Barraja; Alessandra Montalbano
Journal:  Top Curr Chem (Cham)       Date:  2021-08-10
  10 in total

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