title: Alkoxide-induced ring opening of bicyclic 2-vinylcyclobutanones: A convenient synthesis of 2-vinyl-substituted 3-cycloalkene-1-carboxylic acid esters.
abstract: The fused 2-vinyl or 2-phenyl substituted cyclobutanones 4 undergo stereoselective ring openings by the action of alkoxide ions (t-BuO(-) or MeO(-)) to produce novel vicinally disubstituted cycloalkene derivatives 5 and 6 in moderate to high yields. The ring cleavage usually occurs with complete regioselectivity. The accessibility of γ,δ-unsaturated ester or acid derivatives makes this transformation a good supplementary method for the well-established Johnson-Claisen rearrangement.
authors.affiliation: Department of Chemistry, Fudan University, 220 Handan Road, 200433 Shanghai, P. R. China.
authors.forename: Xiufang
authors.initials: X
authors.lastname: Ji
authors.forename: Zhiming
authors.initials: Z
authors.lastname: Li
authors.forename: Quanrui
authors.initials: Q
authors.lastname: Wang
authors.forename: Andreas
authors.initials: A
authors.lastname: Goeke