Convenient Cleavage of Water-Insoluble Allylic Substrates in the Presence of Per(2,6-di-O-methyl)-β-cyclodextrin

Rodrigue Widehem; Thibaut Lacroix; Hervé Bricout; Eric Monflier

doi:10.1055/s-2000-6607

Synlett 2000; 2000(5): 0722-0724
DOI: 10.1055/s-2000-6607

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Convenient Cleavage of Water-Insoluble Allylic Substrates in the Presence of Per(2,6-di-O-methyl)-β-cyclodextrin

Rodrigue Widehem^* , Thibaut Lacroix, Hervé Bricout, Eric Monflier

^*Université d'Artois, Laboratoire de Physico-Chimie des Interfaces et Applications, Faculté des Sciences J. Perrin, Rue J. Souvraz, SP 18 - 62307 Lens Cedex, France; Fax 33 3 21 79 17 55; E-mail: monflier@univ-artois.fr

Abstract

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The removal of allylic protecting groups promoted by a water soluble palladium complex of the trisulfonated triphenylphosphine is achieved in very high yields (95-100%) on a wide range of water-insoluble substrates in a genuine two-phase system by using the per(2,6-di-O-methyl)-β-cyclodextrin as inverse phase transfer catalyst. The catalytic activities were up to 1000 times higher than those observed without cyclodextrin.

cyclodextrin - phase-transfer catalysis - palladium - cleavage - allylic compounds

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