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

09 February 2024, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

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

Keywords

gem-difluorinated cyclopropanes
rhodium catalysis
allylation reaction
enantioselectivity
branched regioselectivity

Supplementary materials

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Supporting Information
Description
Detailed experimental procedures, characterization data, copies of 1H, 13C, 19F NMR and HPLC spectra of products are reported in the Supporting Information.
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