title: α-Arylation and Ring Expansion of Annulated Cyclobutanones: Stereoselective Synthesis of Functionalized Tetralones.
abstract: α-Arylcyclobutanones display unique reactivity that makes them valuable synthetic intermediates and target molecules. We describe the preparation of α-aryl- and α-heteroarylcyclobutanones through a direct α-arylation reaction. Problematic fragmentations are avoided by the use of LiOtBu, which promotes a rapid but reversible self-aldol reaction that slowly releases the enolate required for α-arylation. We also demonstrate the ring expansion of α-arylcyclobutanones, a process that is highlighted in the stereoselective synthesis of 1-methoxy coniothyrinone D.
authors.affiliation: Department of Chemistry, Simon Fraser University, Burnaby, British Columbia, V5A 1S6, Canada.
authors.forename: Stanley
authors.initials: S
authors.lastname: Chang
authors.affiliation: Department of Chemistry, Simon Fraser University, Burnaby, British Columbia, V5A 1S6, Canada.
authors.forename: Michael
authors.initials: M
authors.lastname: Holmes
authors.affiliation: Department of Chemistry, Simon Fraser University, Burnaby, British Columbia, V5A 1S6, Canada.
authors.forename: Jeffrey
authors.initials: J
authors.lastname: Mowat
authors.affiliation: Department of Chemistry, Simon Fraser University, Burnaby, British Columbia, V5A 1S6, Canada.
authors.forename: Michael
authors.initials: M
authors.lastname: Meanwell
authors.affiliation: Department of Chemistry, Simon Fraser University, Burnaby, British Columbia, V5A 1S6, Canada.
authors.forename: Robert
authors.initials: R
authors.lastname: Britton
keywords: cyclobutanones; homogeneous catalysis; ring expansion; synthetic methods; α-arylation