title: Stereocontrolled Syntheses of Seven-Membered Carbocycles by Tandem Allene Aziridination/[4+3] Reaction.
abstract: A tandem allene aziridination/[4+3]/reduction sequence converts simple homoallenic sulfamates into densely functionalized aminated cycloheptenes, where the relative stereochemistry at five contiguous asymmetric centers can be controlled through the choice of the solvent and the reductant. The products resulting from this chemistry can be readily transformed into complex molecular scaffolds which contain up to seven contiguous stereocenters.
authors.affiliation: Department of Chemistry, University of Wisconsin-Madison, 1101 University Avenue, Madison, WI, 53706, USA.
authors.forename: Nels C
authors.initials: NC
authors.lastname: Gerstner
authors.affiliation: Department of Chemistry, University of Wisconsin-Madison, 1101 University Avenue, Madison, WI, 53706, USA.
authors.forename: Christopher S
authors.initials: CS
authors.lastname: Adams
authors.affiliation: Department of Chemistry, University of Wisconsin-Madison, 1101 University Avenue, Madison, WI, 53706, USA.
authors.forename: Maik
authors.initials: M
authors.lastname: Tretbar
authors.affiliation: Department of Chemistry, University of Wisconsin-Madison, 1101 University Avenue, Madison, WI, 53706, USA. schomakerj@chem.wisc.edu.
authors.forename: Jennifer M
authors.identifier: 0000-0003-1329-950X
authors.initials: JM
authors.lastname: Schomaker
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D001388:Aziridines / Q000737:chemistry*; D003500:Cyclization; D003508:Cycloheptanes / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D010084:Oxidation-Reduction; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D001388:Aziridines; D003508:Cycloheptanes
keywords: allenes; cycloaddition; heterocycles; rhodium; synthetic methods