Issue 74, 2017

Synthetic route to chiral indolines via Cu(OAc)2-catalyzed ring-opening/C(sp2)–H activation of activated aziridines

Abstract

A simple strategy for the synthesis of highly functionalized indolines via Lewis acid catalyzed ring-opening of activated aziridines with various nucleophiles followed by Cu(OAc)2-mediated intramolecular C–H amination in one-pot has been developed with excellent enantio- and diastereospecificity (ee 99%; de >99%). The reaction proceeds via Cu(OAc)2-catalyzed SN2-type ring-opening of 2-phenyl-N-(2-pyridinesulfonyl)aziridine with alcohols and arene, followed by copper-mediated pyridine-2-sulfonamide directed intramolecular C(sp2)–H activation/cyclization in a stepwise fashion to furnish the indoline derivatives in excellent yields (up to 91%).

Graphical abstract: Synthetic route to chiral indolines via Cu(OAc)2-catalyzed ring-opening/C(sp2)–H activation of activated aziridines

Supplementary files

Article information

Article type
Communication
Submitted
16 Jul 2017
Accepted
16 Aug 2017
First published
17 Aug 2017

Chem. Commun., 2017,53, 10263-10266

Synthetic route to chiral indolines via Cu(OAc)2-catalyzed ring-opening/C(sp2)–H activation of activated aziridines

A. Mal, G. Goswami, I. Ahmad Wani and M. K. Ghorai, Chem. Commun., 2017, 53, 10263 DOI: 10.1039/C7CC05513G

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