A stereoselective reduction of dibenzo-18-crown-6 ether to dicyclohexyl-18-crown-6 ether |
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| Institution: | 1. Departamento de Química, Universidad de los Andes, Cr. 1 No. 18A 10, Bogotá 111711, Colombia;2. U. D. Química Física, Universidad de Alcalá, 28871 Alcalá de Henares-Madrid, Spain;3. Universidad Nacional de Colombia, Sede Bogotá, Facultad de Ciencias, Departamento de Química, Carrera 30 No. 45-03, Bogotá, Colombia;1. Université de Toulouse, UPS, LHFA, 118 route de Narbonne, F-31062 Toulouse Cedex 9, France;2. CNRS, LHFA UMR 5069, 118 route de Narbonne, F-31062 Toulouse Cedex 9, France;3. Université de Toulouse, UPS, Institut de Chimie de Toulouse FR2599, 118 route de Narbonne, 31062 Toulouse Cedex 9, France |
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| Abstract: | Dibenzo-18-crown-6 ether is reduced to dicyclohexano-18-crown-6 ether under very mild conditions (room temperature and atmospheric hydrogen pressure) in the presence of rhodium salt and phase-transfer reagents. Control over the stereoselectivity of the reduction can be achieved through the proper choice of the phase-transfer agent. Moreover, at higher pressure, the stereoselectivity can be increased up to a 95/5 ratio of the syn/anti isomers of the dicyclohexano-18-crown-6 ether. |
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