Synfacts 2008(4): 0410-0410  
DOI: 10.1055/s-2008-1042822
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Zirconium-Promoted Epoxide Rearrangement-Alkynylation Sequence

Contributor(s): Paul Knochel, Andrei Gavryushin
B. J. Albert, K. Koide*
University of Pittsburg, USA
Further Information

Publication History

Publication Date:
19 March 2008 (online)


The alkynylation of electrophiles is a convenient method for the introduction of a functionalized carbon chain into a molecule. In this work, the authors elegantly combined the Lewis acid promoted epoxide rearrangement with the nucleophilic addition of an acetylide to the resulting aldehyde, thus obtaining propargylic alcohol as the final product. This method is quite simple to perform and offers broad functional group compatibility.