One-pot β-substitution of enones with alkyl groups to β-alkyl enones

Jun-ichi Matsuo, Yayoi Aizawa
2005 Chemical Communications  
General. Infrared (IR) spectra were recorded on a Jasco FT300 FT/IR-420. 1 H NMR spectra were recorded on a JEOL JNM ECP500 (500 MHz) spectrometer; chemical shifts (δ) are reported in parts per million relative to tetramethylsilane. Splitting patterns are designated as s, singlet; d, doublet; t, triplet; q, quartet; m, multiplet; br, broad. 13 C NMR spectra were recorded on a JEOL JNM ECP500 (125 MHz ) spectrometer with complete proton decoupling. Chemical shifts are reported in parts per
more » ... in parts per million relative to tetramethylsilane with the solvent resonance as the internal standard (CDCl 3 ; δ 77.0 ppm). GC-Mass spectra were recorded on a Shimadzu GC-MS QP5050A by chemical ionization method using isobutane. Mass spectra (EI) were recorded on a JEOL JMS-AX505HA in Kitasato University. High resolution mass spectra (HRMS) were recorded on a JEOL JMS-700 mass spectrometer in Kitasato University. Analytical gas-liquid chromatography (GLC) was performed on a Shimadzu GC-18A instrument equipped with a flame ionizing detector and a capillary column of TC-WAX (0.25 mm I.D. x 30 m, df = 0.25um, GL Sciences Inc.) using naphthalene as an internal standard. Analytical TLC was performed on Merck precoated TLC plates (silica gel 60 GF254, 0.25 mm). Silica-gel column chromatography was carried out on silica gel 60N (Kanto Kagaku Co., Ltd., spherical, neutral, 63-210 µm). Preparative thin-layer chromatography (PTLC) was carried out on silica gel Wakogel B-5F. Diethyl ether was
doi:10.1039/b502134k pmid:15877141 fatcat:mymbalgijzahzevziea5pagkxe