title: Studies on the enantioselective catalysis of photochemically promoted transformations: "sensitizing receptors" as chiral catalysts.
abstract: A strategy for the enantioselective catalysis of photomediated reactions in solution is described, involving the use of chiral molecular receptors possessing appendant triplet-sensitizing moieties. Energy transfer is selectively directed to bound substrate as a consequence of the distance dependence of triplet-triplet energy transfer. This effect, which is equivalent to a binding-induced rate enhancement, enables substoichiometric chirality transfer from the receptor template to the substrate, as observed in the intramolecular enone-olefin photo[2 + 2]cycloaddition of a quinolone substrate.
authors.affiliation: Department of Chemistry and Biochemistry, University of Texas at Austin, Austin, Texas 78712, USA.
authors.forename: David F
authors.initials: DF
authors.lastname: Cauble
authors.forename: Vincent
authors.initials: V
authors.lastname: Lynch
authors.forename: Michael J
authors.initials: MJ
authors.lastname: Krische
mesh_terms: D001577:Benzophenones / Q000138:chemical synthesis*; D001665:Binding Sites; D002384:Catalysis; D018360:Crystallography, X-Ray; D003500:Cyclization; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D008024:Ligands; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D008968:Molecular Conformation; D015394:Molecular Structure; D010777:Photochemistry; D015363:Quinolones / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D001577:Benzophenones; D006571:Heterocyclic Compounds; D008024:Ligands; D015363:Quinolones