By Roger A. Sheldon (auth.), Renato Ugo (eds.)

ISBN-10: 9400983719

ISBN-13: 9789400983717

ISBN-10: 9400983735

ISBN-13: 9789400983731

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Example text

Cumene). ), further reaction of the epoxide product with ROzH is rarely observed. 8). 4. 1. , were the most effective catalysts. g. molybdenum metal [107,108], Mo0 3 [75,81,109,110] and molybdic acid [75,81], their activity was generally assumed to result from their dissolution in the presence of the hydroperoxide. The implication was that the reaction occurs in the liquid phase and involves homogeneous catalysis. Thus, in the original examples [75] metal oxides, such as Mo0 3 , were usually given a pretreatment step in which the oxide was heated with tert-butyl hydroperoxide in tert-butanol, in order to effect solubilization of the catalyst.

Much progress has been made in recent years in the area of asymmetric hydrogenation [173], for example. In contrast, little has been achieved in the area of asymmetric oxidations. An efficient method for the asymmetric epoxidation of olefins could prove to be an invaluable synthetic tool. Two groups [112,174] of workers chose the facile vanadium- and molybdenum-catalysed epoxidations of allylic alcohols as a model reaction for the study of asymmetric epoxidations. Yamada el at. [174] used the chiral molybdenum catalyst (XLI) for the epoxidation of allylic alcohols with cumene hydroperoxide.

When the chlorine is attached directly to the double bond (vinylic chloride) no epoxidation occurs [143]. Epoxidation is not seriously impeded by the presence of electron-attracting groups when they are sufficiently removed from the double bond. For example, 4-cyanocyclohexene is smoothly epoxidized to give an 89% yield of the epoxide (Eq. 79) [15]. Cyanomethylcyclohexene gave a moderate yield [82,83], whilst acrylonitrile gave no reaction at all. OCN R0 2 H Mo (VI) .. oOCN (79) 89% ()CN .. , j3-unsaturated esters, such as ethyl methacrylate [82,83].

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Aspects of Homogeneous Catalysis by Roger A. Sheldon (auth.), Renato Ugo (eds.)


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