A High Cis-Stereoselectivity in the Hydrogenation of 6-t-Butyltetrahydropyran-3-one and 2-t-Butyl-1, 3-dioxan-5-one

…, T Terasawa, J Ishiyama, S Kamiyama…

Index: Senda; Terasawa; Ishiyama; Kamiyama; Imaizumi Bulletin of the Chemical Society of Japan, 1989 , vol. 62, # 9 p. 2948 - 2952

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Citation Number: 11

Abstract

Stereochemistry in the hydrogenation of 4-t-butylcyclohexanone and the corresponding oxa- and dioxacyclohexanone was examined. A high cis selectivity was observed in the latter two compounds regardless of the catalyst metals used here. These results were explained in terms of intramolecular n O–π CO interaction, which was supported by 13 C NMR chemical shifts of the carbonyl carbons and CNDO/2 calculation.