Tetrahedron letters

An efficient synthesis of 1-phenyl-1-piperidino-trans-4-methylcyclohexane: Unanticipated total stereoselectivity in the catalytic hydrogenation of an olefin

FJ Vinick, J Nowakowska, S Jung

Index: Vinick, F.J.; Nowakowska, J.; Jung, S. Tetrahedron Letters, 1987 , vol. 28, # 7 p. 741 - 744

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Citation Number: 1

Abstract

Abstract A superior synthesis of the title compound, 1-phenyl-1-piperidino-trans-4- methylcyclohexane, is reported. The key step, the catalytic hydrogenation of 1-phenyl-1- piperidino-4-methylenecyclohexane hydrochloride, proceeds with unusual stereospecificity via addition of hydrogen trans to the axial phenyl substituent.