THE REACTION OF TRIALKYLSTANNYLMETHYLLITHIUM WITH α,β-EPOXY KETONES. A PREPARATIVE METHOD OF β,γ-UNSATURATED KETONES BY HOMOLOGATION OF α,β-UNSATURATED KETONES

Article abstract of DOI:10.1016/S0040-4039(00)98963-9

α,β-Epoxy ketones 2, upon treatment with two equivalents of trialkylstannylmethyllithium 1, afforded cyclopropanols 3 as a single product in acyclic system, and a mixture of cyclopropanols 3 and methylene 1,2-diols 4 in cyclic system.Under acidic conditions, the cyclopropanols gave β,γ-unsaturated ketones 5 in good yields.