Issue 34, 2016

Iridium-catalyzed asymmetric [3+2] annulation of aromatic ketimines with alkynes via C–H activation: unexpected inversion of the enantioselectivity induced by protic acids

Abstract

A cationic iridium/binap catalyst enabled the asymmetric [3+2] annulation of cyclic N-acyl ketimines with internal alkynes via C–H activation to give spiroaminoindene derivatives with high enantioselectivity. The stereochemical course of this annulation was switchable by acid additives.

Graphical abstract: Iridium-catalyzed asymmetric [3+2] annulation of aromatic ketimines with alkynes via C–H activation: unexpected inversion of the enantioselectivity induced by protic acids

Supplementary files

Article information

Article type
Communication
Submitted
15 Feb 2016
Accepted
29 Mar 2016
First published
29 Mar 2016
This article is Open Access
Creative Commons BY license

Chem. Commun., 2016,52, 5876-5879

Iridium-catalyzed asymmetric [3+2] annulation of aromatic ketimines with alkynes via C–H activation: unexpected inversion of the enantioselectivity induced by protic acids

M. Nagamoto, D. Yamauchi and T. Nishimura, Chem. Commun., 2016, 52, 5876 DOI: 10.1039/C6CC01398H

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