Issue 4, 2014
From the journal:

Organic Chemistry Frontiers

Intermolecular bromoesterification of conjugated enynes: an efficient synthesis of bromoallenes†

Hao-Yuan Wang,a   Wei Zhang,a   Casi M. Schienebeck,a   Scott R. Bennetta  and  Weiping Tang*ab  

* Corresponding authors

a School of Pharmacy, University of Wisconsin, Madison, WI, USA

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

Abstract

We have discovered that bromine electrophile and carboxylate nucleophile can be added to conjugated enynes intermolecularly in a 1,4-fashion with high diastereoselectivity. Highly functionalized bromoallenes with an adjacent stereogenic centre were prepared from readily available conjugated 1,3-enynes.

Graphical abstract: Intermolecular bromoesterification of conjugated enynes: an efficient synthesis of bromoallenes

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Article information

DOI
https://doi.org/10.1039/C3QO00088E
Article type
Research Article
Submitted
31 Dec 2013
Accepted
08 Mar 2014
First published
20 Mar 2014

Org. Chem. Front., 2014,1, 386-390

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Intermolecular bromoesterification of conjugated enynes: an efficient synthesis of bromoallenes

H. Wang, W. Zhang, C. M. Schienebeck, S. R. Bennett and W. Tang, Org. Chem. Front., 2014, 1, 386 DOI: 10.1039/C3QO00088E

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