Ruthenium catalyzed cycloisomerization of silicon-tethered 1,7-enynes to give exocyclic 1,3-dienes.

Org Lett

Department of Chemistry, 1-014 Center for Science and Technology, Syracuse University, Syracuse, New York 13244, United States.

Published: October 2014

The cycloisomerization of vinyl silicon-tethered 1,7-enynes has been accomplished using catalytic Cp*Ru(COD)Cl. The products possess a new silane moiety and trisubstituted alkenes as part of the diene system. The reaction scope includes aryl, alkyl, vinyl, and cyclopropyl alkyne functionalities. Silicon was found not to be a mandatory component of the tether. The utility of the products was demonstrated through manipulation of the vinyl silane and Diels-Alder chemistry.

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http://dx.doi.org/10.1021/ol5026926DOI Listing

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