Literature DB >> 22497267

Enantioselective synthesis of dihydropyrazoles by formal [4+1] cycloaddition of in situ-derived azoalkenes and sulfur ylides.

Jia-Rong Chen1, Wan-Rong Dong, Mathieu Candy, Fang-Fang Pan, Manuel Jörres, Carsten Bolm.   

Abstract

An unprecedented strategy to access highly enantioenriched dihydropyrazoles is described. It involves formal [4+1] cycloadditions of in situ-derived azoalkenes and sulfur ylides catalyzed by a chiral copper/Tol-BINAP complex. A variety of synthetically and biologically important dihydropyrazoles have been obtained with high enantioselectivities (up to 97:3 er) in good yields (83-97%).

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Year:  2012        PMID： 22497267     DOI： 10.1021/ja301196x

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  10 in total

1.  Catalytic Asymmetric [3+1]-Cycloaddition Reaction of Ylides with Electrophilic Metallo-enolcarbene Intermediates.

Authors:  Yongming Deng; Lynée A Massey; Peter Y Zavalij; Michael P Doyle
Journal:  Angew Chem Int Ed Engl       Date:  2017-05-22       Impact factor: 15.336

2.  Bond-Forming and -Breaking Reactions at Sulfur(IV): Sulfoxides, Sulfonium Salts, Sulfur Ylides, and Sulfinate Salts.

Authors:  Daniel Kaiser; Immo Klose; Rik Oost; James Neuhaus; Nuno Maulide
Journal:  Chem Rev       Date:  2019-06-25       Impact factor: 60.622

3.  One-pot sequential synthesis of tetrasubstituted thiophenes via sulfur ylide-like intermediates.

Authors:  Jun Ki Kim; Hwan Jung Lim; Kyung Chae Jeong; Seong Jun Park
Journal:  Beilstein J Org Chem       Date:  2018-01-26       Impact factor: 2.883

Review 4.  Sulfur-Based Ylides in Transition-Metal-Catalysed Processes.

Authors:  James D Neuhaus; Rik Oost; Jérémy Merad; Nuno Maulide
Journal:  Top Curr Chem (Cham)       Date:  2018-04-13

5.  A Catalytic Cross-Olefination of Diazo Compounds with Sulfoxonium Ylides.

Authors:  James D Neuhaus; Adriano Bauer; Alexandre Pinto; Nuno Maulide
Journal:  Angew Chem Int Ed Engl       Date:  2018-11-08       Impact factor: 15.336

6.  Mild synthesis of isoxazoline derivatives via an efficient [4 + 1] annulation reaction of transient nitrosoalkenes and sulfur ylides.

Authors:  Ting-Bi Hua; Cheng-Xiong Liu; Wei-Min Hu; Long Wang; Qing-Qing Yang
Journal:  Sci Rep       Date:  2021-01-22       Impact factor: 4.379

7.  Formal [4 + 1] cycloaddition of in situ generated 1,2-diaza-1,3-dienes with diazo esters: facile approaches to dihydropyrazoles containing a quaternary center.

Authors:  Bo Chen; Wen-Dao Chu; Quan-Zhong Liu
Journal:  RSC Adv       Date:  2019-01-11       Impact factor: 4.036

8.  Protecting group-directed annulations of tetra-substituted oxindole olefins and sulfur ylides: regio- and chemoselective synthesis of cyclopropane- and dihydrofuran-fused spirooxindoles.

Authors:  Jing-Wen Kang; Xiang Li; Fei-Yu Chen; Yuan Luo; Shu-Cang Zhang; Bin Kang; Cheng Peng; Xu Tian; Bo Han
Journal:  RSC Adv       Date:  2019-04-17       Impact factor: 4.036

9.  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

10.  Mn- and Co-Catalyzed Aminocyclizations of Unsaturated Hydrazones Providing a Broad Range of Functionalized Pyrazolines.

Authors:  Moritz Balkenhohl; Sebastian Kölbl; Tony Georgiev; Erick M Carreira
Journal:  JACS Au       Date:  2021-06-11
  10 in total

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