Issue 16, 2012
From the journal:

Chemical Communications

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

Suyu Huang,ab   Xiaoxun Li,b   Claire L. Lin,b   Ilia A. Guzeic  and  Weiping Tang*b  

* Corresponding authors

a Department of Chemistry and Key Laboratory for Chemical Biology of Fujian Province, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian, PR China

b School of Pharmacy, University of Wisconsin, Madison, WI, USA
E-mail: wtang@pharmacy.wisc.edu

c Department of Chemistry, University of Wisconsin, Madison, WI, USA

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

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Article information

DOI
https://doi.org/10.1039/C2CC17406E
Article type
Communication
Submitted
28 Nov 2011
Accepted
22 Dec 2011
First published
04 Jan 2012

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

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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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