Lewis Acid Catalyzed Stereoselective Dearomative Coupling of Indolylboron Ate Complexes with Donor-Acceptor Cyclopropanes and Alkyl Halides.

Saikat DasConstantin G DaniliucArmido Studer

Published in: Angewandte Chemie (International ed. in English) (2018)

Indolylboron ate complexes readily generated from 2-lithioindoles and boronic esters underwent multicomponent dearomative coupling with D-A cyclopropanes and alkyl halides in the presence of Sc(OTf)3 as a catalyst. The reactions proceeded with complete diastereoselectivity and excellent stereospecificity to provide indolines containing three contiguous stereocenters. The valuable boronic ester moiety remains in the product and allows for subsequent functionalization.

Keyphrases

room temperature
ionic liquid
visible light
solar cells
energy transfer
electron transfer