Stereoselective synthesis of cyclopropanone ketals via silyl chloride promoted cyclization of β-zinciopropionates

Article abstract of DOI:10.1016/0040-4020(95)00331-2

Alkyl, allyl, and propargyl β-iodopropionates undergo a cyclopropanation by the reaction with zinc-copper couple and TBDMSCI in THF to give 1-alkoxy-, 1-allyloxy- and 1-propargyloxy-1-tert-butyldimethylsiloxycyclopropanes in moderate or good yields. β-Iodo-α-methylpropionates 2 and 6 provide trans-5 and trans-8 selectively, which β-iodobutyrates 3 and 7 furnish cis-5 and cis-8 selectively.