A new zincate-mediated rearrangement reaction of 2-(1-hydroxyalkyl)-1-alkylcyclopropanol.
A novel rearrangement of 2-(1-hydroxyalkyl)-1-alkylcyclopropanol has been found. It proceeds in the presence of a catalytic amount of organozinc ate complex to give vic-diols. The rearrangement can be applied to various types of 2-(1-hydroxyalkyl)-1-alkylcyclopropanol, which can be easily prepared from the corresponding alpha,beta-epoxyketones and bis(iodozincio)methane. When bicyclo[13.1.0]pentadecane-1,15-diol was treated with the organozinc ate complex, the corresponding 14-membered cyclic vic-diol was obtained. Thus, this rearrangement is also useful for changing the ring size of cyclic substrates.
Nomura
Kenichi
K
Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoutodaigaku-katsura, Nishikyo-ku, Kyoto 615-8510, Japan.
Matsubara
Seijiro
S