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Relaying stereochemistry through aromatic ureas: 1,9 and 1,15 remote stereocontrol

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  • Chemistry


but exp 1 Relaying stereochemistry through aromatic ureas: 1,9 and 1,15 remote stereocontrol Jonathan Clayden,* Mark Pickworth and Lyn H. Jones SUPPORTING INFORMATION General Information NMR spectra were recorded on a Varian XL 300 or a Bruker Ultrashield 300, 400 or 500 spectrometer. The chemical shifts (δ) are reported in ppm downfield of trimethylsilane and coupling constants (J) reported in hertz and rounded to 0.5 Hz. Splitting patterns are abbreviated as follows: singlet (s), doublet (d), triplet (t), quartet (q), multiplet (m), broad (br), or a combination of these. Solvents were used as internal standard when assigning NMR spectra (δH: CDCl3 7.27 ppm; δC: CDCl3 77.0 ppm; δH: DMSO-d6 2.50 ppm; δC: DMSO-d6 39.4 ppm; δH: CD3OD 3.31 ppm; δC: CD3OD 49.0 ppm;). Low and high resolution mass spectra were recorded by staff at the University of Manchester. EI and CI spectra were recorded on a Fisons VG Trio 2000; and high resolution mass spectra (HRMS) were recorded on a Kratos Concept-IS mass spectrometer, and are accurate to ± 0.001. Infrared spectra were recorded on an Ati Matson Genesis Series FTIR spectrometer as a film on a sodium chloride plate. Absorptions reported are sharp and strong unless otherwise stated as broad (br), medium (m), or weak (w), only absorption maxima of interest are reported. Melting points (mpt) were determined on a Gallenkamp apparatus and are uncorrected. Thin layer chromatography (TLC) was performed using commercially available pre-coated plates (Macherey- Nagel alugram Sil G/UV254) and visualised with UV light at 254 nm or phosphomolybdic acid dip (5 % in ethanol). Flash chromatography was carried out using Fluorochem Davisil 40-63u 60 Å. All reactions were conducted under an atmosphere of dry nitrogen in oven dried glassware. Tetrahydrofuran (THF) was distilled under nitrogen from sodium using benzophenone as indicator. Dichloromethane and toluene were obtained by distil

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