title: Copper-mediated aerobic synthesis of 3-azabicyclo[3.1.0]hex-2-enes and 4-carbonylpyrroles from N-allyl/propargyl enamine carboxylates.
abstract: Synthetic methods for 3-azabicyclo[3.1.0]hex-2-enes and 4-carbonylpyrroles have been developed that use copper-mediated/catalyzed reactions of N-allyl/propargyl enamine carboxylates under an O(2) atmosphere and involve intramolecular cyclopropanation and carbooxygenation, respectively. These methodologies take advantage of orthogonal modes of chemical reactivity of readily available N-allyl/propargyl enamine carboxylates; the complementary pathways can be accessed by slight modification of the reaction conditions.
authors.affiliation: Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore, Singapore.
authors.forename: Kah Kah
authors.initials: KK
authors.lastname: Toh
authors.forename: Yi-Feng
authors.initials: YF
authors.lastname: Wang
authors.forename: Eileen Pei Jian
authors.initials: EP
authors.lastname: Ng
authors.forename: Shunsuke
authors.initials: S
authors.lastname: Chiba
mesh_terms: D001643:Bridged Bicyclo Compounds / Q000737:chemistry*; D002264:Carboxylic Acids / Q000737:chemistry*; D002384:Catalysis; D060326:Chemistry Techniques, Synthetic / Q000379:methods; D003300:Copper / Q000737:chemistry*; D010100:Oxygen / Q000737:chemistry; D010293:Pargyline / Q000031:analogs & derivatives* / Q000737:chemistry*; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D001643:Bridged Bicyclo Compounds; D002264:Carboxylic Acids; D011758:Pyrroles; D003300:Copper; D010293:Pargyline; D010100:Oxygen