title: A tunable route for the synthesis of azomethine imines and β-aminocarbonyl compounds from alkenes.
abstract: Cyclic azomethine imines possessing a β-aminocarbonyl motif are accessed from simple alkene and hydrazone starting materials. A thermal, concerted alkene aminocarbonylation pathway involving an imino-isocyanate intermediate is proposed and supported by DFT calculations. A notable feature of the process is the steric shielding present in the dipoles formed, which allows for facile purification of the products by chromatography or crystallization. In addition, a fluorenone-derived reagent is reported, which provides reactivity with several alkene classes and allows for mild derivatization of the dipoles into β-aminoamides, β-aminoesters, and β-amino acids.
authors.affiliation: Centre for Catalysis Research and Innovation, Department of Chemistry, University of Ottawa, 10 Marie Curie, Ottawa, Ontario, Canada, K1N 6N5.
authors.forename: Christian
authors.initials: C
authors.lastname: Clavette
authors.forename: Wei
authors.initials: W
authors.lastname: Gan
authors.forename: Amanda
authors.initials: A
authors.lastname: Bongers
authors.forename: Thomas
authors.initials: T
authors.lastname: Markiewicz
authors.forename: Amy B
authors.initials: AB
authors.lastname: Toderian
authors.forename: Serge I
authors.initials: SI
authors.lastname: Gorelsky
authors.forename: André M
authors.initials: AM
authors.lastname: Beauchemin
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D001391:Azo Compounds / Q000737:chemistry*; D060326:Chemistry Techniques, Synthetic; D006835:Hydrazones / Q000737:chemistry; D007097:Imines / Q000138:chemical synthesis* / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry; D013882:Thiosemicarbazones / Q000737:chemistry*
chemical_list: D000475:Alkenes; D001391:Azo Compounds; D006835:Hydrazones; D007097:Imines; D007659:Ketones; D013882:Thiosemicarbazones; C512188:azomethine