Enantioselective Arylation of 3-Carboxamide Oxindoles with Quinone Monoimines and Synthesis of Chiral Spirooxindole-benzofuranones-Reference-Cited by-同舟云学术

Enantioselective Arylation of 3-Carboxamide Oxindoles with Quinone Monoimines and Synthesis of Chiral Spirooxindole-benzofuranones

Published:2019-04-02 Issue:09 Volume:30 Page:1067-1072
ISSN:0936-5214
Container-title:Synlett
language:en
Short-container-title:Synlett

Author:

Chen Hui¹²,Liu Hui¹²,Zhao Si-Han¹²,Cheng Shao-Bing¹²,Xu Xiao-Ying¹,Yuan Wei-Cheng¹,Zhang Xiao-Mei¹^ORCID

Affiliation:

1. Key Laboratory for Asymmetric Synthesis & Chirotechnology of Sichuan Province, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences

2. University of Chinese Academy of Sciences

Abstract

A highly enantioselective arylation of 3-carboxamide oxoindoles with quinone monoimines is described. Various 3-aryl-3-carboxamide oxindoles with an all-carbon quaternary center were obtained in moderate to good yields (up to 99%) with moderate to good enantioselectivities (up to 98%) in the presence of a bifunctional thiourea-tertiary amine catalyst. The absolute configuration of one product was determined by an X-ray crystal structural analysis and the absolute configurations of the other products can be assigned by analogy. Moreover, several chiral spirooxindole-benzofuranones were synthesized from the 3-aryl-3-carboxamide oxindoles in moderate yields with moderate to good enantioselectivities.

Funder

National Natural Science Foundation of China

Publisher

Georg Thieme Verlag KG

Subject

Organic Chemistry

Link

http://www.thieme-connect.de/products/ejournals/pdf/10.1055/s-0037-1611782.pdf

Cited by 8 articles. 订阅此论文施引文献订阅此论文施引文献，注册后可以免费订阅5篇论文的施引文献，订阅后可以查看论文全部施引文献

1. Synthesis of novel benzothieno-[3,2’-f][1,3] oxazepines and their isomeric 2-oxo-2H-spiro[benzothiophene-3,3’-pyrrolines] via 1,4-dipolar cycloaddition reaction and their evaluation as cytotoxic anticancer leads;Medicinal Chemistry Research;2024-05-11

2. Organocatalytic asymmetric [3 + 3] annulations of 3-carboxamide oxindoles with β,γ-unsaturated α-keto esters: facile access to chiral spiro-δ-lactam oxindoles;Organic Chemistry Frontiers;2023

3. Chiral Primary Amine Catalyzed α ‐Arylation of Simple Ketones via Asymmetric Retro‐Claisen Cleavage;Chemistry – A European Journal;2022-10-27

4. Iron-Catalyzed Oxidative Cross-Coupling of Phenols and Tyrosine Derivatives with 3-Alkyloxindoles;The Journal of Organic Chemistry;2021-12-09

5. 3-Carboxamide oxindoles as 1,3-C,N-bisnucleophiles for the highly diastereoselective synthesis of CF3-containing spiro-δ-lactam oxindoles featuring acyl at the ortho-position of spiro carbon atom;Tetrahedron Letters;2021-10