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Lewis Acid Catalyzed Stereoselective Dearomative Coupling of Indolylboron Ate Complexes with Donor–Acceptor Cyclopropanes and Alkyl Halides
Author(s) -
Das Saikat,
Daniliuc Constantin G.,
Studer Armido
Publication year - 2018
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201711923
Subject(s) - moiety , stereocenter , chemistry , alkyl , halide , stereospecificity , stereoselectivity , catalysis , lewis acids and bases , boronic acid , organic chemistry , medicinal chemistry , combinatorial chemistry , stereochemistry , enantioselective synthesis
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.