Literature DB >> 27600647

Construction of Quaternary Stereocenters by Nickel-Catalyzed Heck Cyclization Reactions.

Jean-Nicolas Desrosiers1, Liana Hie2, Soumik Biswas3, Olga V Zatolochnaya3, Sonia Rodriguez3, Heewon Lee3, Nelu Grinberg3, Nizar Haddad3, Nathan K Yee3, Neil K Garg2, Chris H Senanayake3.   

Abstract

A nickel-catalyzed Heck cyclization for the construction of quaternary stereocenters is reported. This transformation is demonstrated in the synthesis of 3,3-disubstituted oxindoles, which are prevalent motifs seen in numerous biologically active molecules. The method shows broad scope, proceeds in synthetically useful yields, and provides a rare means to construct stereochemically complex frameworks by nonprecious-metal catalysis.
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  Heck reaction; cyclization; heterocycles; homogeneous catalysis; nickel

Year:  2016        PMID： 27600647     DOI： 10.1002/anie.201606955

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  8 in total

1.  Breaking Amides using Nickel Catalysis.

Authors:  Jacob E Dander; Neil K Garg
Journal:  ACS Catal       Date:  2017-01-06       Impact factor: 13.084

2.  Mizoroki-Heck Cyclizations of Amide Derivatives for the Introduction of Quaternary Centers.

Authors:  Jose M Medina; Jesus Moreno; Sophie Racine; Shuaijing Du; Neil K Garg
Journal:  Angew Chem Int Ed Engl       Date:  2017-05-03       Impact factor: 15.336

3.  Nickel-Catalyzed Enantioselective Conjunctive Cross-Coupling of 9-BBN Borates.

Authors:  Matteo Chierchia; Chunyin Law; James P Morken
Journal:  Angew Chem Int Ed Engl       Date:  2017-08-17       Impact factor: 15.336

4.  Enantioselective Nickel-Catalyzed Mizoroki-Heck Cyclizations To Generate Quaternary Stereocenters.

Authors:  Jean-Nicolas Desrosiers; Jialin Wen; Sergei Tcyrulnikov; Soumik Biswas; Bo Qu; Liana Hie; Dmitry Kurouski; Ling Wu; Nelu Grinberg; Nizar Haddad; Carl A Busacca; Nathan K Yee; Jinhua J Song; Neil K Garg; Xumu Zhang; Marisa C Kozlowski; Chris H Senanayake
Journal:  Org Lett       Date:  2017-06-12       Impact factor: 6.005

5.  Nickel-Catalyzed Enantioselective Reductive Alkyl-Carbamoylation of Internal Alkenes.

Authors:  Xianqing Wu; Aneta Turlik; Baixue Luan; Feng He; Jingping Qu; K N Houk; Yifeng Chen
Journal:  Angew Chem Int Ed Engl       Date:  2022-07-25       Impact factor: 16.823

6.  Ni-catalysed regioselective 1,2-diarylation of unactivated olefins by stabilizing Heck intermediates as pyridylsilyl-coordinated transient metallacycles.

Authors:  Surendra Thapa; Roshan K Dhungana; Rajani Thapa Magar; Bijay Shrestha; Shekhar Kc; Ramesh Giri
Journal:  Chem Sci       Date:  2017-11-27       Impact factor: 9.825

7.  Diastereoselective Synthesis of N-Methylspiroindolines by Intramolecular Mizoroki-Heck Annulations.

Authors:  Jens Lindman; Greeshma Gopalan; Carlos Palo-Nieto; Peter Brandt; Johan Gising; Mats Larhed
Journal:  ACS Omega       Date:  2022-08-26

8.  Synthesis of Spiroindenyl-2-Oxindoles through Palladium-Catalyzed Spirocyclization of 2-Bromoarylamides and Vinyl Bromides.

Authors:  Shuai Yang; Yanghui Zhang
Journal:  Molecules       Date:  2021-12-10       Impact factor: 4.411
  8 in total

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