Issue 1, 2011

Rhodium catalyzed allene amidation: a facile entry into 2-amidoallylcations for unusual [3 + 3] annulation reactions

Abstract

The interaction of a sulfamate ester derived metallonitrene with an allene generates a versatile intermediate with 2-amidoallylcation like reactivity. In this article we outline reactivity patterns for this novel dipolar species, demonstrating both [3 + 2] reactions with benzaldehyde, and unusual [3 + 3] annulation reactions with a variety of nitrones.

Graphical abstract: Rhodium catalyzed allene amidation: a facile entry into 2-amidoallylcations for unusual [3 + 3] annulation reactions

Supplementary files

Article information

Article type
Edge Article
Submitted
16 Jul 2010
Accepted
17 Aug 2010
First published
16 Sep 2010

Chem. Sci., 2011,2, 112-116

Rhodium catalyzed allene amidation: a facile entry into 2-amidoallylcations for unusual [3 + 3] annulation reactions

A. H. Stoll and S. B. Blakey, Chem. Sci., 2011, 2, 112 DOI: 10.1039/C0SC00375A

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