title: Formal intramolecular (4 + 1)-cycloaddition of dialkoxycarbenes: control of the stereoselectivity and a mechanistic portrait.
abstract: The stereoselective synthesis of 5-5, 6-5, and 7-5 fused O-heterocyclic compounds is reported. The key reaction is a formal intramolecular (4 + 1)-cycloaddition involving a dialkoxycarbene and an electron-deficient diene where the stereoselectivity is dependent on the length of the tether. An analysis of the stereochemical outcome of this reaction sheds light on its complex mechanistic picture. High-level calculations were used to support the proposed mechanistic portrait.
authors.affiliation: Département de Chimie, Université de Sherbrooke, 2500 Boul. Université, Sherbrooke, Quebec, Canada J1K 2R1.
authors.forename: Francis
authors.initials: F
authors.lastname: Beaumier
authors.forename: Marianne
authors.initials: M
authors.lastname: Dupuis
authors.forename: Claude
authors.initials: C
authors.lastname: Spino
authors.forename: Claude Y
authors.initials: CY
authors.lastname: Legault