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Issue 1, 2011
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Rhodium catalyzed allene amidation: a facile entry into 2-amidoallylcations for unusual [3 + 3] annulation reactions

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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

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Article information


Submitted
16 Jul 2010
Accepted
17 Aug 2010
First published
16 Sep 2010

Chem. Sci., 2011,2, 112-116
Article type
Edge Article

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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