Lc esi it tof ms equipment

IR spectra were determined on a JASCO FT/IR-4100 spectrometer. Exact mass (HRMS) spectra were recorded on JMS-HX mass spectrometer or Shimadzu LC-ESI-IT-TOF-MS equipment. 1 H NMR spectra were recorded using a JEOL ECA-400 or JEOL ECA-500 spectrometer at a 500 MHz frequency. Chemical shifts are reported in δ (ppm) relative to Me4Si (in CDCl3) as an internal standard. 13 C NMR spectra were recorded using a JEOL ECA-500 unit and referenced to the residual solvent signal. Melting points were measured by a hot stage melting point apparatus (uncorrected). For column chromatography, silica gel (Wakogel C-200E: Wako Pure Chemical Industries, Ltd) or amine silica gel (CHROMATOREX NH-DM1020: Fuji Silysia Chemical Ltd.) was employed. Chiral chromatography was performed with a Cosmosil CHiRAL 5B column (4.6 mm × 250 mm, Nacalai Tesque Inc.) or CHIRALCEL OD-H column (4.6 mm × 250 mm, Daicel Inc.) with using n-hexane/i-PrOH as an eluent. The gold complexes (R)-DTBM-SEGPHOS(AuCl)2, (S)-DTBM-SEGPHOS(AuCl)2, (R)-DTBM-BINOL(AuCl)2, and (R)-DADMP-BINOL(AuCl)2 were prepared according to the literature. 18, 19

General Methods 1 H-NMR spectra were recorded using a JEOL ECA-500 spectrometer at 500 MHz frequency. Chemical shifts are reported in δ (ppm) relative to Me 4 Si (in CDCl 3 ) as internal standard. 13 (link) C-NMR spectra were recorded using a JEOL ECA-500 and referenced to the residual CHCl 3 signal. Exact mass (HR-MS) spectra were recorded on a Shimadzu LC-ESI-IT-TOF-MS equipment (electrospray ionization (ESI)). Optical rotations were measured with a JASCO P-1020 polarimeter. For column chromatography, Wakogel C-300E (Wako, Osaka, Japan) or Chromatorex NH-DM1020 (Fuji Silysia, Japan) was employed.

1 H NMR spectra were recorded using a JEOL AL-400 or a JEOL ECA-500 spectrometer. Chemical shifts are reported in δ (ppm) relative to Me4Si as an internal standard. 13 C NMR spectra were recorded using a JEOL AL-400 or a JEOL ECA-500 and referenced to the residual solvent signal. Exact mass (HRMS) spectra were recorded on Shimadzu LC-ESI-IT-TOF-MS equipment. IR spectra were obtained on a JASCO FT/IR-4100 spectrometer. Melting points were measured by a hot stage melting points apparatus (uncorrected). Optical rotations were measured with a JASCO P-1020 polarimeter.
For chromatography, Wakogel C-300E (Wako) was employed. (158 mg, 1.00 mmol) in EtOH (2.00 mL) was added quinoline-2-carbohydrazide [28] (187 mg, 1.00 mmol). After being stirred for 17 h at 70 °C, the reaction mixture was concentrated. The residue was dissolved with EtOAc, and the whole was washed with 1 M NaOH and brine, and dried over Na2SO4.
After the filtrate was concentrated, the residue was purified by column chromatography on silica gel (n-hexane/EtOAc = 1/3) to give the title compound 6 (107 mg, 26%): pale yellow amorphous solid;
[α] 24