Asymmetric epoxidation of alkenes using a mixed-ligand complex of ruthenium(III) containing a sugar-based ligand |
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| Authors: | Debabrata Chatterjee Susan Basak Ayon Sengupta Jacques Muzart |
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| Institution: | a Chemistry Section, Central Mechanical Engineering Research Institute, MG Avenue, Durgapur 713 209, West Bengal, India
b Unité Mixte de Recherche ‘Réactions Sélectives et Applications’, CNRS-Université de Reims Champagne-Ardenne, BP 1039, 51687 Reims cedex 2, France |
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| Abstract: | A mixed-ligand ruthenium(III) catalyst complex, RuIII(TDL*)(bipy)(H2O)]Cl (1) (TDL* = N-3,5-di-(t-butyl)salicylidine-d-glucosamine; bipy = 2,2′-bipyridine) exhibited catalytic activity toward enantioselective alkene epoxidation using tert-butyl hydroperoxide as terminal oxidant. Styrene, 4-chlorostyrene, 4-methylstyrene, 4-methoxystyrene, 1-methylcyclohexene and 1,2-dihydronaphthalene were effectively converted to their organic epoxides with moderate enantioselectivity (37-47% ee) at ambient temperature. A mechanism involving the formation of a high-valent Ru(V)-oxo species, and the subsequent oxo-transfer to the alkene through a metallaoxetane intermediate is proposed. |
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| Keywords: | Ruthenium complex Sugar-based ligand t-BuOOH Styrenes Epoxidation Enantioselectivity Alkenes |
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