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

Autor: Senda, Yasuhisa, Terasawa, Toshiyuki, Ishiyama, Jun-ichi, Kamiyama, Shin-ichi, Imaizumi, Shin
Zdroj: Bulletin of the Chemical Society of Japan; September 1989, Vol. 62 Issue: 9 p2948-2952, 5p
Abstrakt: 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 nO–πCOinteraction, which was supported by 13C NMR chemical shifts of the carbonyl carbons and CNDO/2 calculation.
Databáze: Supplemental Index