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Synthesis 2007(20): 3252-3256  
DOI: 10.1055/s-2007-983831
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© Georg Thieme Verlag Stuttgart · New York

Synthesis of 1,5-Enynes by Brønsted Acid Catalyzed Substitution of Propargylic Alcohols and One-Pot Synthesis of Bicyclo[3.1.0]hexenes

Roberto Sanz*a, Alberto Martíneza, Delia Miguela, Julia M. Álvarez-Gutiérreza, Félix Rodríguez*b
a Departamento de Química, Área de Química Orgánica, Facultad de Ciencias, Universidad de Burgos, Pza. Misael Bañuelos s/n, 09001-Burgos, Spain
Fax: +34(947)258831; e-Mail: rsd@ubu.es;
b Instituto Universitario de Química Organometálica ‘Enrique Moles’, Universidad de Oviedo, C/ Julián Clavería 8, 33006-Oviedo, Spain
Fax: +34(98)5103447; e-Mail: frodriguez@uniovi.es;
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Publication History

Received 12 March 2007
Publication Date:
30 July 2007 (online)

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Abstract

A practical air and moisture tolerant procedure for the preparation of 1,5-enynes from propargylic alcohols by the Brønsted acid catalyzed direct propargylic substitution of the hydroxy group with allylsilanes is described. Also, a straightforward sequential catalytic protocol for the synthesis of bicyclo[3.1.0]hexane derivatives, from readily available starting materials, is presented.

Key words

catalysis - allylations - alcohols - enynes - tandem reactions

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In some cases, and when refluxing conditions are required, competitive formation of the corresponding symmetric ether is observed (ca. 20% isolated yield).