Literature DB >> 26991133

Copper/Guanidine-Catalyzed Asymmetric Alkynylation of Isatins.

Quangang Chen1, Yu Tang1, Tianyu Huang1, Xiaohua Liu2, Lili Lin1, Xiaoming Feng1,3.   

Abstract

The highly enantioselective alkynylation of isatins, catalyzed by a bifunctional guanidine/CuI catalyst under mild reaction conditions, is described. The reaction is broad in scope with respect to alkyl/aryl-substituted terminal alkynes and substituted isatins, thus affording bioactive propargylic alcohols in excellent yields and enantioselectivities.
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  alkynes; asymmetric catalysis; copper; heterocycles; ligand design

Year:  2016        PMID： 26991133     DOI： 10.1002/anie.201600711

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


  7 in total

1.  Catalytic Enantioselective Ynamide Additions to Isatins: Concise Access to Oxindole Alkaloids.

Authors:  Max Moskowitz; Christian Wolf
Journal:  Angew Chem Int Ed Engl       Date:  2019-02-14       Impact factor: 15.336

Review 2.  Recent Advances in Catalytic Alkyne Transformation via Copper Carbene Intermediates.

Authors:  Kuiyong Dong; Mengting Liu; Xinfang Xu
Journal:  Molecules       Date:  2022-05-11       Impact factor: 4.927

3.  Distal Stereocontrol Using Guanidinylated Peptides as Multifunctional Ligands: Desymmetrization of Diarylmethanes via Ullman Cross-Coupling.

Authors:  Byoungmoo Kim; Alex J Chinn; Daniel R Fandrick; Chris H Senanayake; Robert A Singer; Scott J Miller
Journal:  J Am Chem Soc       Date:  2016-06-15       Impact factor: 15.419

4.  PdII on Guanidine-Functionalized Fe3O4 Nanoparticles as an Efficient Heterogeneous Catalyst for Suzuki-Miyaura Cross-Coupling and Reduction of Nitroarenes in Aqueous Media.

Authors:  Guddappa Halligudra; Chitrabanu C Paramesh; Ravi Mudike; Mallesha Ningegowda; Dinesh Rangappa; Prasanna D Shivaramu
Journal:  ACS Omega       Date:  2021-12-09

5.  Enantioselective [1,2]-Stevens rearrangement of thiosulfonates to construct dithio-substituted quaternary carbon centers.

Authors:  Linfeng Hu; Jinzhao Li; Yongyan Zhang; Xiaoming Feng; Xiaohua Liu
Journal:  Chem Sci       Date:  2022-03-11       Impact factor: 9.825

6.  Copper-catalyzed enantioselective Sonogashira-type oxidative cross-coupling of unactivated C(sp3)-H bonds with alkynes.

Authors:  Zhen-Hua Zhang; Xiao-Yang Dong; Xuan-Yi Du; Qiang-Shuai Gu; Zhong-Liang Li; Xin-Yuan Liu
Journal:  Nat Commun       Date:  2019-12-12       Impact factor: 14.919

7.  Enantioselective carbene insertion into the N-H bond of benzophenone imine.

Authors:  Jian Yang; Peiran Ruan; Wei Yang; Xiaoming Feng; Xiaohua Liu
Journal:  Chem Sci       Date:  2019-09-18       Impact factor: 9.825
  7 in total

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