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Brønsted Acid-Promoted Intramolecular Carbocyclization of Alkynals Leading to Cyclic Enones

Carlos González-Rodríguez, Luz Escalante, Jesús A. Varela, Luis Castedo and Carlos Sáa*

*Departamento de Química Orgánica, Facultad de Química, Universidad de Santiago de Compostela, 15782 Santiago de Compostela, Spain, Email: carlos.saausc.es

C. González-Rodríguez, L. Escalante, J. A. Varela, L. Castedo, C. Sáa, Org. Lett., 2009, 11, 1531-1533.

DOI: 10.1021/ol900142r (free Supporting Information)


Abstract

TFA-promoted exo carbocyclizations of nonterminal alkynals gave good to excellent yields of exo cycloalkenones. On the other hand, terminal 5-alkynals gave endo carbocyclizations to cyclohexenones. These carbocyclizations can be considered as tandem alkyne hydration/aldol condensation processes.

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Ru-Catalyzed Cyclization of Terminal Alkynals to Cycloalkenes

J. A. Varela, C. González-Rodríguez, S. G. Rubín, L. Castedo, Carlos Saá, J. Am. Chem. Soc., 2006, 128, 9576-9577.


Key Words

endo Cyclohexenones, Cyclopentenes, Cyclohexenes, Cycloheptenes


ID: J54-Y2009-1050