Optically active silyl and stannyl substituted cyclopropylmethanols were effectively obtained by the catalytic and enantioselective cyclopropanation of gamma-silyl and gamma-stannyl substituted allylic alcohols with Et(2)Zn and CH2I2 in the presence of chiral N,N'-bis(p-nitrobenzenesulfonyl) -1,2 -cyclohexanediamine in goad enantioselectivites. The absolute configurations of the resulting metallocyclopropanes were unambiguously established.