title: [2+2] Photocycloaddition of Cinnamates in Flow and Development of a Thiourea Catalyst.
abstract: Cyclobutanes derived from the dimerization of cinnamic acids are the core scaffolds of many molecules with potentially interesting biological activities. By utilizing a powerful flow photochemistry platform developed in our laboratory, we have evaluated the effects of flow on the dimerization of a range of cinnamate substrates. During the course of the study we also identified a bis(thiourea) catalyst that facilitates better reactivity and moderate diastereoselectivity in the reaction. Overall, we show that carrying out the reaction in flow in the presence of the catalyst affords consistent formation of predictable cyclobutane diastereomers.
authors.affiliation: Department of Chemistry, Boston University, 590 Commonwealth Ave. Boston, MA 02215 (USA).
authors.forename: Reem
authors.initials: R
authors.lastname: Telmesani
authors.affiliation: Department of Chemistry, Boston University, 590 Commonwealth Ave. Boston, MA 02215 (USA).
authors.forename: Sung H
authors.initials: SH
authors.lastname: Park
authors.affiliation: Department of Chemistry, Boston University, 590 Commonwealth Ave. Boston, MA 02215 (USA).
authors.forename: Tessa
authors.initials: T
authors.lastname: Lynch-Colameta
authors.affiliation: Department of Chemistry, Boston University, 590 Commonwealth Ave. Boston, MA 02215 (USA). beelera@bu.edu.
authors.forename: Aaron B
authors.initials: AB
authors.lastname: Beeler
mesh_terms: D002384:Catalysis; D002934:Cinnamates / Q000737:chemistry*; D061565:Cycloaddition Reaction; D019281:Dimerization; D055668:Photochemical Processes; D066244:Proton Magnetic Resonance Spectroscopy; D013890:Thiourea / Q000737:chemistry*
chemical_list: D002934:Cinnamates; D013890:Thiourea
keywords: cinnamates; cyclobutanes; flow chemistry; photochemistry; truxinates