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Remote stereocontrol in reactions between 4- and 5-alkoxyalk-2-enylstannanes and 1-alkoxycarbonylimines and analogues: stereoselective approaches to novel a-aminoacids

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  • Chemistry

Abstract

Microsoft Word - Supplementary experimental.docx Remote stereocontrol in reactions between 4- and 5-alkoxyalk-2- enylstannanes and 1-alkoxycarbonylimines and analogues: stereoselective approaches to novel α-amino acids David J. Hallett,a Nongluk Tanikkula and Eric J. Thomasa* Supplementary experimental General experimental procedures NMR spectra were obtained using Varian Unity 500, Bruker AC 300, or Varian XL 300 spectrometers. Chemical shifts are quoted in parts per million downfield from tetramethylsilane. Low resolution MS were obtained on a Fisons VG Trio 2000 spectrometer, using electron impact (EI) and chemical ionisation (CI) modes. Fast atom bombardment (FAB) and high resolution mass measurements were acquired on a Kratos Concept spectrometer. IR spectra were measured on an ATI Mattson Genesis Series FTIR spectrometer as evaporated thin films on sodium chloride plates. Optical rotations were measured at 589 nm at ambient temperature using an Optical Activity AA-100 polarimeter. All non-aqueous reactions were performed in oven (140 °C) or flame-dried glassware under an inert atmosphere of dry nitrogen or argon. Solvents were dried immediately prior to use by distillation under an atmosphere of dry nitrogen from sodium benzophenone ketyl (diethyl ether, tetrahydrofuran, hexane), calcium hydride (DCM, dimethyl sulfoxide) or anhydrous potassium hydroxide (triethylamine, diisopropylamine, pyridine). Analytical grade toluene and benzene were dried over sodium wire for 24 hours prior to use. Methanol was dried over magnesium turnings and then distilled. Petrol refers to that fraction of light petroleum ether which boils between 40 and 60 °C and was redistilled prior to use. Butyllithium was supplied as a solution in hexanes and was titrated against anhydrous butanol in tetrahydrofuran using 2,2'-dipyridyl as indicator. Ether refers to diethyl ether whilst brine refers to saturated aqueous sodium chloride. Preparative column chromatography was carried o

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