Issue 12, 2015

Enantioselective gold catalyzed dearomative [2+2]-cycloaddition between indoles and allenamides

Abstract

The highly enantioselective synthesis of densely functionalized 2,3-indoline-cyclobutanes by means of chiral gold catalysis is presented. Intermolecular formal [2+2]-cycloaddition reactions between substituted indoles and allenamides enabled direct access to methylenecyclobutane-fused indolines, featuring two consecutive quaternary stereogenic centers with excellent stereochemical control (dr > 20 : 1, ee up to 99%).

Graphical abstract: Enantioselective gold catalyzed dearomative [2+2]-cycloaddition between indoles and allenamides

Supplementary files

Article information

Article type
Communication
Submitted
03 Nov 2014
Accepted
20 Dec 2014
First published
22 Dec 2014

Chem. Commun., 2015,51, 2320-2323

Enantioselective gold catalyzed dearomative [2+2]-cycloaddition between indoles and allenamides

M. Jia, M. Monari, Q. Yang and M. Bandini, Chem. Commun., 2015, 51, 2320 DOI: 10.1039/C4CC08736D

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