Advanced Synthesis and Catalysis
Advanced Synthesis and Catalysis
5 years ago

Gold-Catalyzed Cycloisomerizations of Functionalyzed Cyclopropyl Alkynes: the Cases of Carboxamides and Alcohols

Gold-Catalyzed Cycloisomerizations of Functionalyzed Cyclopropyl Alkynes: the Cases of Carboxamides and Alcohols
Patricia García-García, Isabel Merino, Jesús M. Fernández-García, Manuel A. Fernández-Rodríguez, Laura Fernández-García, Enrique Aguilar, Hugo A. Garro
Push-pull alkynylcyclopropane derivatives are claimed as suitable and active substrates for gold-catalyzed transformations. Thus, 2(3H)-azepinones can be readily prepared from alkynylcyclopropanecarboxamides through a nucleophilic addition/cyclopropane ring-opening cascade process and, in this manuscript, the scope and the limitations of such reaction sequence are reported. The cascade reaction is general and occurs with complete regio- and quimioselection to form the seven-membered heterocycles with the exception of primary alkyl-substituted alkynylcyclopropanecarboxamides that render 4-methoxy-6-oxo-4-enenitriles in moderate yields. Additionally, less activated alkynylcyclopropylmethanols undergo regioselective cycloisomerization at low temperature leading to oxabicyclo[4.1.0]heptanes. Notably, the cyclopropane ring opening of these adducts takes place under thermal conditions to form dihydropyranones.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/adsc.201700264

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