Regiodivergent catalytic asymmetric dearomative cycloaddition of bicyclic heteroaromatics

Author:

Peng Lei1ORCID,Zeng Zhen2ORCID,Li Kai1ORCID,Liu Yidong1ORCID,Lan Yu23ORCID,Yan Hailong1ORCID

Affiliation:

1. Chongqing Key Laboratory of Natural Product Synthesis and Drug Research, Chemical Biology Research Center, School of Pharmaceutical Sciences, Chongqing University, Chongqing, China.

2. Chongqing Key Laboratory of Theoretical and Computational Chemistry, School of Chemistry and Chemical Engineering, Chongqing University, Chongqing, China.

3. Green Catalysis Center, College of Chemistry, Zhengzhou University, Zhengzhou, China.

Abstract

The catalytic dearomative cycloaddition of bicyclic heteroaromatics including benzofurans and indoles provides rapid access to functionalized heterocyclic molecules. Because of the inherent stereoelectronic differences, the furan or pyrrole nucleus is more prone to dearomative cycloaddition than the benzene ring. Here, we realized a geometry-based differentiation approach for achieving C6-C7 and C7-C7a regioselectivity. The rotationally restricted σ bond at C7 position respectively placed the C6-C7 and C7-C7a sites of benzofurans or indoles in an optimal spatial orientation toward the axially chiral heterodiene, thus affording two enantioenriched polycyclic compounds from a single racemic heterobiaryl atropisomers. Calculation results of density functional theory interpreted the mechanism of this parallel kinetic resolution. The bioactivity of the dearomatized products was evaluated in cancer cell lines with certain compounds exhibiting interesting biological activities.

Publisher

American Association for the Advancement of Science (AAAS)

Subject

Multidisciplinary

同舟云学术

1.学者识别学者识别

2.学术分析学术分析

3.人才评估人才评估

"同舟云学术"是以全球学者为主线,采集、加工和组织学术论文而形成的新型学术文献查询和分析系统,可以对全球学者进行文献检索和人才价值评估。用户可以通过关注某些学科领域的顶尖人物而持续追踪该领域的学科进展和研究前沿。经过近期的数据扩容,当前同舟云学术共收录了国内外主流学术期刊6万余种,收集的期刊论文及会议论文总量共计约1.5亿篇,并以每天添加12000余篇中外论文的速度递增。我们也可以为用户提供个性化、定制化的学者数据。欢迎来电咨询!咨询电话:010-8811{复制后删除}0370

www.globalauthorid.com

TOP

Copyright © 2019-2024 北京同舟云网络信息技术有限公司
京公网安备11010802033243号  京ICP备18003416号-3