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; Alberto Martínez; Delia Miguel; Julia M. Álvarez-Gutiérrez; Félix Rodríguez

doi:10.1055/s-2007-983831

PSP

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 Martínez^a, Delia Miguel^a, Julia M. Álvarez-Gutiérrez^a, 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;

Abstract

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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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References

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