Issue 16, 2012

Rhodium-catalyzed 1,3-acyloxy migration and subsequent intramolecular [4+2] cycloaddition of vinylallene and unactivated alkyne

Abstract

A Rh-catalyzed 1,3-acyloxy migration of propargyl ester followed by intramolecular [4+2] cycloaddition of vinylallene and unactivated alkyne was developed. This tandem reaction provides access to bicyclic compounds containing a highly functionalized isotoluene or cyclohexenone structural motif, while only aromatic compounds were observed in related transition metal-catalyzed cycloadditions.

Graphical abstract: Rhodium-catalyzed 1,3-acyloxy migration and subsequent intramolecular [4+2] cycloaddition of vinylallene and unactivated alkyne

Supplementary files

Article information

Article type
Communication
Submitted
28 Nov 2011
Accepted
22 Dec 2011
First published
04 Jan 2012

Chem. Commun., 2012,48, 2204-2206

Rhodium-catalyzed 1,3-acyloxy migration and subsequent intramolecular [4+2] cycloaddition of vinylallene and unactivated alkyne

S. Huang, X. Li, C. L. Lin, I. A. Guzei and W. Tang, Chem. Commun., 2012, 48, 2204 DOI: 10.1039/C2CC17406E

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