Synthesis of Cyclohexanones through a Catalytic Cationic Cyclization of Alkynols or Enynes
Pedro Alonso, Raquel Fontaneda, Pilar Pardo, Francisco J. Fañanás* and Félix Rodríguez*
*Instituto Universitario de Química Organometálica "Enrique
Moles", Universidad de Oviedo, Julián Clavería 8, E-33006 Oviedo, Spain, Email:
fjfv
uniovi.es, frodriguezuniovi.es
P. Alsonso, R. Fonteneda, P. Pardo, F. J. Fañanás, F. Rodríguez, Org. Lett., 2018, 20, 1659-1662.
DOI: 10.1021/acs.orglett.8b00437
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Abstract
A cationic cyclization enables the synthesis of cyclohexanones from alkynol or enyne derivatives with a terminal triple bond. Crucial for the success of the reaction are the use of tetrafluoroboric acid as a promoter of the cationic cyclization, and the selection of 1,1,1,3,3,3-hexafluoropropan-2-ol as solvent. This strategy can be extended to the biomimetic cationic cyclization of several terpene-derived polyenynes.
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Key Words
ID: J54-Y2018
