title: Copper(II)-Promoted Cyclization/Difunctionalization of Allenols and Allenylsulfonamides: Synthesis of Heterocycle-Functionalized Vinyl Carboxylate Esters.
abstract: A unique method to affect intramolecular aminooxygenation and dioxygenation of allenols and allenylsulfonamides is described. These operationally simple reactions occur under neutral or basic conditions where copper(II) carboxylates serve as reaction promoter, oxidant, and carboxylate source. Moderate to high yields of heterocycle-functionalized vinyl carboxylate esters are formed with moderate to high levels of diastereoselectivity. Such vinyl carboxylate esters could serve as precursors to α-amino and α-oxy ketones and derivatives thereof.
authors.affiliation: Department of Chemistry, Natural Science Complex, The State University of New York at Buffalo , Buffalo, New York 14260, United States.
authors.forename: Barbara J
authors.initials: BJ
authors.lastname: Casavant
authors.affiliation: Department of Chemistry, Natural Science Complex, The State University of New York at Buffalo , Buffalo, New York 14260, United States.
authors.forename: Zainab M
authors.initials: ZM
authors.lastname: Khoder
authors.affiliation: Department of Chemistry, Natural Science Complex, The State University of New York at Buffalo , Buffalo, New York 14260, United States.
authors.forename: Ilyas A
authors.initials: IA
authors.lastname: Berhane
authors.affiliation: Department of Chemistry, Natural Science Complex, The State University of New York at Buffalo , Buffalo, New York 14260, United States.
authors.forename: Sherry R
authors.initials: SR
authors.lastname: Chemler
mesh_terms: D000466:Alkadienes / Q000737:chemistry*; D002264:Carboxylic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D003300:Copper / Q000737:chemistry*; D003500:Cyclization; D004952:Esters; D009682:Magnetic Resonance Spectroscopy; D008698:Mesylates / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism; D013449:Sulfonamides / Q000737:chemistry*; D014297:Trimethylsilyl Compounds / Q000737:chemistry
chemical_list: D000466:Alkadienes; D002264:Carboxylic Acids; D004952:Esters; D008698:Mesylates; D013449:Sulfonamides; D014297:Trimethylsilyl Compounds; C053353:trimethylsilyl trifluoromethanesulfonate; D003300:Copper