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Ru-Catalyzed Cyclization of Terminal Alkynals to Cycloalkenes

Jesús A. Varela, Carlos González-Rodríguez, Silvia G. Rubín, Luis Castedo and Carlos Saá*

*Departamento de Química Orgánica y Unidad Asociada al CSIC, Facultad de Química, Universidad de Santiago de Compostela, 15782 Santiago de Compostela, Spain, Email: qocsaausc.es

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

DOI: 10.1021/ja0610434 (free Supporting Information)


Abstract

Cycloalkenes can be efficiently prepared by a new Ru-catalyzed decarbonylative cyclization of terminal alkynals. Under appropriate conditions, cycloisomerizations to conjugated aldehydes may be observed. Both processes involve catalytic Ru vinylidenes.


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proposed mechanism



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

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


Key Words

Cycloalkenes, Cyclopentenes, Cyclohexenes


ID: J48-Y2006-2280