title: Dynamic kinetic asymmetric [3 + 2] annulation reactions of aminocyclopropanes.
abstract: We report the first example of a dynamic kinetic asymmetric [3 + 2] annulation reaction of aminocyclopropanes with both enol ethers and aldehydes. Using a Cu catalyst and a commercially available bisoxazoline ligand, cyclopentyl- and tetrahydrofurylamines were obtained in 69-99% yield and up to a 98:2 enantiomeric ratio using the same reaction conditions. The method gives access to important enantio-enriched nitrogen building blocks for the synthesis of bioactive compounds.
authors.affiliation: Laboratory of Catalysis and Organic Synthesis, Ecole Polytechnique Fédérale de Lausanne, EPFL SB ISIC LCSO , BCH 4306, 1015 Lausanne, Switzerland.
authors.forename: Florian
authors.initials: F
authors.lastname: de Nanteuil
authors.forename: Eloisa
authors.initials: E
authors.lastname: Serrano
authors.forename: Daniele
authors.initials: D
authors.lastname: Perrotta
authors.forename: Jerome
authors.initials: J
authors.lastname: Waser
mesh_terms: D000447:Aldehydes / Q000138:chemical synthesis / Q000737:chemistry*; D000586:Amination; D000588:Amines / Q000138:chemical synthesis / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry; D018360:Crystallography, X-Ray; D003521:Cyclopropanes / Q000138:chemical synthesis / Q000737:chemistry*; D007700:Kinetics; D008958:Models, Molecular; D010080:Oxazoles / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D000588:Amines; D003521:Cyclopropanes; D010080:Oxazoles; D003300:Copper