Catalytic Enantioselective Synthesis of 2,3'-Bis(indolyl)methanes Bearing All-Carbon Quaternary Stereocenters via 2-Indole Imine Methides

Zhengyu Han; Wenlong Wang; Han Zhuang; Jie Wang; Cheng Wang; Jianhao Wang; Hai Huang; Jianwei Sun

doi:10.1021/acs.orglett.2c04109

Catalytic Enantioselective Synthesis of 2,3'-Bis(indolyl)methanes Bearing All-Carbon Quaternary Stereocenters via 2-Indole Imine Methides

Org Lett. 2023 Jan 27;25(3):477-482. doi: 10.1021/acs.orglett.2c04109. Epub 2023 Jan 15.

Authors

Zhengyu Han¹, Wenlong Wang¹, Han Zhuang¹, Jie Wang¹, Cheng Wang², Jianhao Wang², Hai Huang¹, Jianwei Sun^{1

3}

Affiliations

¹ Jiangsu Key Laboratory of Advanced Catalytic Materials & Technology, School of Petrochemical Engineering, Changzhou University, Changzhou 213164, China.
² School of Pharmacy, Changzhou University, Changzhou 213164, China.
³ Department of Chemistry, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong SAR, China.

PMID: 36641768
DOI: 10.1021/acs.orglett.2c04109

Abstract

An organocatalytic enantioselective formal hydroarylation of 2-vinyl indoles for the preparation of enantioenriched 2,3'-bis(indolyl)methanes bearing an all-carbon quaternary stereocenter is described. This reaction features mild conditions, low catalyst loading, excellent efficiency and enantioselectivity. The obtained products showed promising anticancer activity.