Literature DB >> 30480863

Catalytic Atropenantioselective Heteroannulation between Isocyanoacetates and Alkynyl Ketones: Synthesis of Enantioenriched Axially Chiral 3-Arylpyrroles.

Sheng-Cai Zheng1, Qian Wang1, Jieping Zhu1.   

Abstract

We report herein the first examples of catalytic enantioselective synthesis of axially chiral 3-arylpyrroles. Reaction of α-isocyanoacetates with β-aryl-α,β-alkynic ketones in the presence of silver oxide and a phosphine ligand derived from Cinchona alkaloid occurred chemoselectively to afford enantioenriched 3-arylpyrroles in high yields with excellent enantiomeric excesses. The pyrrole ring was constructed de novo in this process.
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  arylpyrrole; asymmetric synthesis; axial chirality; homogeneous catalysis; isocyanide

Year:  2018        PMID: 30480863     DOI: 10.1002/anie.201812654

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


  4 in total

1.  Conversion of two stereocenters to one or two chiral axes: atroposelective synthesis of 2,3-diarylbenzoindoles.

Authors:  Yu-Long Hu; Zhe Wang; Hui Yang; Jie Chen; Zi-Bo Wu; Yibo Lei; Ling Zhou
Journal:  Chem Sci       Date:  2019-05-20       Impact factor: 9.825

2.  AgNTf2-catalyzed formal [3 + 2] cycloaddition of ynamides with unprotected isoxazol-5-amines: efficient access to functionalized 5-amino-1H-pyrrole-3-carboxamide derivatives.

Authors:  Ziping Cao; Jiekun Zhu; Li Liu; Yuanling Pang; Laijin Tian; Xuejun Sun; Xin Meng
Journal:  Beilstein J Org Chem       Date:  2019-11-04       Impact factor: 2.883

3.  Bidirectional enantioselective synthesis of bis-benzofuran atropisomeric oligoarenes featuring two distal C-C stereogenic axes.

Authors:  Xiaoze Bao; Jean Rodriguez; Damien Bonne
Journal:  Chem Sci       Date:  2019-11-20       Impact factor: 9.825

4.  Ag2O versus Cu2O in the Catalytic Isomerization of Coordinated Diaminocarbenes to Formamidines: A Theoretical Study.

Authors:  Juan F Van der Maelen; Javier Ruiz
Journal:  Materials (Basel)       Date:  2022-01-10       Impact factor: 3.623

  4 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.