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Dearomative Diallylation of N-Acylindoles Mediated by FeCl3

Author:
Wu, Ju, Nandi, Raj Kumar, Guillot, Régis, Kouklovsky, Cyrille, Vincent, Guillaume
Source:
Organic letters 2018 v.20 no.7 pp. 1845-1848
ISSN:
1523-7052
Subject:
chemical reactions, ferric chloride, moieties, organic compounds, stereoselectivity
Abstract:
Three-dimensional indolines possessing two contiguous-stereogenic centers were obtained stereoselectively via the FeCl₃-mediated dearomative introduction of two allyl groups to N-acylindoles with allyltrimethylsilane. Synthetic transformations allowed obtention of trans-tetrahydrocarbazoles and an aza[4.4.3]propellane scaffold by RCM. Selective hydration of one of the allyl groups was also achieved.
Agid:
6083673