Enantioselective construction of C-chiral allylic sulfilimines via the iridium-catalyzed allylic amination with S,S-diphenylsulfilimine: asymmetric synthesis of primary allylic amines† †Electronic supplementary information (ESI) available. See DOI: 10.1039/c4sc01317d Click here for additional data file.

1. General Information All reactions were carried out in flame-dried glassware under an atmosphere of argon or nitrogen using anhydrous solvent. Dichloromethane was dried by passage through activated alumina columns. n-Propylamine was distilled from activated zinc dust and stored over sodium hydroxide. All other reagents were purchased from Acros, Aldrich, Alfa Aesar or Strem and used as received. Thin layer chromatography (TLC) was performed using Whatman F254 or EMD Chemicals Inc. 60 F254 precoated silica gel plates. Visualisation was accomplished with a UV light, ceric ammonium nitrate solution or ninhydrin. Flash chromatography was performed using Merck Silica Gel 60 (230-400 mesh), Whatman Silica Gel Purasil 60Å (230-400 mesh) or EMD Silica Gel 60 (0.04 – 0063 mm particle size). The melting points were obtained from a Buchi Melting Point Apparatus. Solvents for extraction and flash chromatography were reagent grade. Infrared spectra were obtained on a Perkin-Elmer spectrum 100 series or an Agilent Technologies Cary 630 FTIR spectrometer. Peaks are reported in cm with the following relative intensities: vs (very strong), s (strong), m (medium) and w (weak). Mass spectra were performed at the University of Liverpool Mass Spectrometry Center, EPSRC National Mass Spectrometry Service Centre or Queen’s University Mass Spectrometry and Proteomics Services Unit. High-resolution electronimpact (EI, ionization voltages of 70 eV) and chemical ionization mass spectra (CI, reagent gas CH4 or NH3) were obtained on either a Micromass 70-250S double focusing mass spectrometer or an Autospec, ZAB 2SE, Kratos MS-80, VG 7070E double focusing magnetic sector mass spectrometer equipped with a solid probe inlet, a Quattro II, MAT 95, or a MAT 900. The electrospray ionization (ESI) mass spectra were obtained on a Waters micromass LCT mass spectrometer. H