title: Cyclooctanoid ring systems from mixed acetals via heteroatom-assisted [1,2]-shift of oxonium ylides.
abstract: Cyclic mixed acetals with pendant diazoketone side chains undergo efficient rearrangement to ether-bridged cyclooctanoid systems upon treatment with Cu(hfacac)2. This result demonstrates that heterosubstituted carbons are suitable migrating groups for the Stevens [1,2]-shift of oxonium ylides. In the case of a mixed thioacetal, the resulting sulfide served as a trigger for cleavage of the bridging ether through one of two complementary strategies, furnishing a bicyclo[6.3.0]octene product with an angular hydroxyl group.
authors.affiliation: Department of Chemistry, University of Alberta, Edmonton, Alberta, Canada T6G 2G2.
authors.forename: Fredrik P
authors.initials: FP
authors.lastname: Marmsäter
authors.forename: Graham K
authors.initials: GK
authors.lastname: Murphy
authors.forename: F G
authors.initials: FG
authors.lastname: West