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Synthesis of Medium-Sized Carbocycles by Gallium-Catalyzed Tandem Carbonyl-Olefin Metathesis/Transfer Hydrogenation

Alexandre Djurovic, Marie Vayer, Zhilong Li, Regis Guillot, Jean-Pierre Baltaze, Vincent Gandon* and Christophe Bour*

*Institut de Chimie Moléculaire et des Matériaux d’Orsay, Université Paris-Sud, Université Paris-Saclay, Bâtiment 420, Orsay 91405 Cedex, France, Email:,

A. Djurovic, M. Vayer, Z. Li, R. Guillot, J.-P. Baltaze, V. Gandon, C. Bour, Org. Lett., 2019, 21, 8132-8137.

DOI: 10.1021/acs.orglett.9b03240

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[IPr·GaCl2][SbF6] catalyzes a tandem process involving a ring-closing carbonyl-olefin metathesis and a transfer hydrogenation in the presence of 1,4-cyclohexadiene as an H2 surrogate to reduce the cyclic alkene intermediates. This stereoselective reaction leads to 1,2-cis-disubstituted cyclopentanes and various cyclohexanes.

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Key Words

cyclopentanes, 1,4-cyclohexadiene

ID: J54-Y2019