title: Gold(i)-catalyzed 6-endo-dig azide-yne cyclization: efficient access to 2H-1,3-oxazines.
abstract: Denitrogenative 6-endo-dig azide-yne cyclization of α-propargyloxy-β-haloalkylazides was enabled by gold catalysis, thus providing 2H-1,3-oxazines. This rare cyclization mode in gold-catalyzed reactions of azide-yne substrates was demonstrated to be facilitated and controlled by electronic and resonance effects of the alkyne substituents. Molecular transformations of the as-prepared 2H-1,3-oxazines were also investigated.
authors.affiliation: Département de Chimie, UMR 7652 and 7653 CNRS, Ecole Polytechnique, 91128 Palaiseau, France.
authors.forename: Geoffroy Hervé
authors.initials: GH
authors.lastname: Lonca
authors.affiliation: Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371, Singapore. shunsuke@ntu.edu.sg.
authors.forename: Ciputra
authors.initials: C
authors.lastname: Tejo
authors.affiliation: Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371, Singapore. shunsuke@ntu.edu.sg.
authors.forename: Hui Ling
authors.initials: HL
authors.lastname: Chan
authors.affiliation: Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371, Singapore. shunsuke@ntu.edu.sg.
authors.forename: Shunsuke
authors.identifier: http://orcid.org/0000-0003-2039-023X
authors.initials: S
authors.lastname: Chiba
authors.affiliation: Département de Chimie, UMR 7652 and 7653 CNRS, Ecole Polytechnique, 91128 Palaiseau, France and Department of Chemistry and Biomolecular Sciences, University of Ottawa, K1N 6N5, Ottawa, Canada. fgagosz@uottawa.ca.
authors.forename: Fabien
authors.initials: F
authors.lastname: Gagosz