Design and Catalytic Asymmetric Synthesis of Furan‐Indole Compounds Bearing both Axial and Central Chirality

Author:

Wang Jing‐Yi1,Gao Cong‐Hui1,Ma Cheng2,Wu Xin‐Yue1,Ni Shao‐Fei2,Tan Wei1,Shi Feng134ORCID

Affiliation:

1. School of Chemistry and Materials Science Jiangsu Normal University Xuzhou 221116 China

2. Department of Chemistry Key Laboratory for Preparation and Application of Ordered Structural Materials of Guangdong Province Shantou University Shantou 515063 China

3. School of Petrochemical Engineering Changzhou University Changzhou 213164 China

4. School of Chemistry and Chemical Engineering Henan Normal University Xinxiang 453007 China

Abstract

AbstractIn the chemistry community, catalytic asymmetric synthesis of furan‐based compounds bearing both axial and central chirality has proven to be a significant but challenging issue owing to the importance and difficulty in constructing such frameworks. In this work, we have realized the first catalytic asymmetric synthesis of five‐five‐membered furan‐based compounds bearing both axial and central chirality via organocatalytic asymmetric (2+4) annulation of achiral furan‐indoles with 2,3‐indolyldimethanols with uncommon regioselectivity. By this strategy, furan‐indole compounds bearing both axial and central chirality were synthesized in high yields with excellent regio‐, diastereo‐, and enantioselectivities. Moreover, theoretical calculations were conducted to provide an in‐depth understanding of the reaction pathway, activation mode, and the origin of the selectivity.

Funder

National Natural Science Foundation of China

Natural Science Foundation of Jiangsu Province

Natural Science Research of Jiangsu Higher Education Institutions of China

Publisher

Wiley

Subject

General Medicine

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