@ARTICLE{Virumbrales20208443,
author={Virumbrales, C. and Suárez-Pantiga, S. and Marín-Luna, M. and Silva López, C. and Sanz, R.},
title={Unlocking the 5-exo Pathway with the Au(I)-Catalyzed Alkoxycyclization of 1,3-Dien-5-ynes},
journal={Chemistry - A European Journal},
year={2020},
volume={26},
number={38},
pages={8443-8451},
doi={10.1002/chem.202001296},
abstract={The first general regio- and stereoselective 5-exo gold(I)-catalyzed alkoxycyclization of a specific class of 1,5-enynes such as 1,3-dien-5-ynes has been described, despite 1,5-enynes being known to almost invariably proceed via endo cyclizations under gold-catalysis. The configuration of the terminal alkene in the starting 1,3-dien-5-yne plays a crucial role on the regiochemical outcome of the reaction. A wide variety of interesting alkoxy-functionalized alkylidenecyclopentenes have been synthesized from 1-monosubstituted (E)-1,3-dien-5-ynes. On the contrary, the corresponding Z isomers evolve affording formal 6-endo cyclization products. In addition, mechanistic exploration supports a highly stabilized carbocation as a key intermediate instead of a highly constrained cyclopropyl gold carbene from E isomers, and also accounts for the well differentiated reactivity observed between both E/Z geometrical isomers as well as for the stereochemical outcome of the reaction.},
}

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