Hydrozirconation of alkenyloxirane derivatives: Preparation of cycloalkylmethanols

Article abstract of DOI:10.1016/S0040-4020(97)10340-4

Cyclopentyl and cyclopropylmethanol derivatives were efficiently prepared through a chemoselective hydrozirconation reaction of (1- butenyl)oxirane and vinyloxirane with Cp₂ZrHCl. However, the attemped reaction of (1-pentenyl)oxirane or (1-propenyl)oxirane failed to yield cyclohexyl or cyclobutylmethanols. The ring formation was stereospecific and proceeded with the inversion of the configuration at the reacting oxirane carbon. The origin of stereospecificity and the stereoselectivity in the formation of cyclopropylmethanols was presumed by the approach of the Schwartz reagent from the less hindered site of the stable gauche-conformer of the vinyloxirane compound in the transition state. (Cyclopropylmethyl)amine derivatives were also prepared by the treatment of vinylaziridine derivatives with Cp₂ZrHCl.