Synthesis of cyclopropanols via cyclopropanation of zinc enolates

Article abstract of DOI:10.1016/S0040-4039(98)01036-3

The reaction of α-iodoketones with diethylzinc afforded zinc enolates which were convened into the corresponding cyclopropanols in good yields upon treatment with CH₂I₂ and Et₂Zn. The use of α-iodoketone having a carbon- carbon double bond as a substrate proved that cyclopropanation of the enolate moiety proceeded chemoselectively. Cyclopropanation of the zinc enolates derived from α,β-unsaturated ketones via 1,4-addition of organozinc species was also achieved.