Rhodium-Catalyzed Enantio- and Regioselective Allylation of Indoles with gem-Difluorinated Cyclopropanes

Hui Yang; Yaxin Zeng; Xiangyu Song; Lin Che; Zhong-Tao Jiang; Gang Lu; Ying Xia

doi:10.1002/anie.202403602

Rhodium-Catalyzed Enantio- and Regioselective Allylation of Indoles with gem-Difluorinated Cyclopropanes

Angew Chem Int Ed Engl. 2024 Mar 22:e202403602. doi: 10.1002/anie.202403602. Online ahead of print.

Authors

Hui Yang¹, Yaxin Zeng¹, Xiangyu Song¹, Lin Che², Zhong-Tao Jiang¹, Gang Lu³, Ying Xia¹

Affiliations

¹ West China School of Public Health and West China Fourth Hospital, and State Key Laboratory of Biotherapy, Sichuan University, Chengdu, 610041, China.
² Linyi University, School of Chemistry and Chemical Engineering, Linyi, 276000, China.
³ School of Chemistry and Chemical Engineering, Key Laboratory of Colloid and Interface Chemistry, Ministry of Education, Shandong University, Jinan, 250100, China.

PMID: 38515395
DOI: 10.1002/anie.202403602

Abstract

The use of gem-difluorinated cyclopropanes (gem-DFCPs) as fluoroallyl surrogates under transition-metal catalysis has drawn considerable attention recently but such reactions are restricted to producing achiral or racemic mono-fluoroalkenes. Herein, we report the first enantioselective allylation of indoles under rhodium catalysis with gem-DFCPs. This reaction shows exceptional branched regioselectivity towards rhodium catalysis with gem-DFCPs, which provides an efficient route to enantioenriched fluoroallylated indoles with wide substrate scope and good functional group tolerance.

Keywords: allylation reactions; enantioselectivity; gem-difluorinated cyclopropanes; regioselectivity; rhodium catalysis.

Abstract

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