Jmtc 400 54 ss

FTIR spectra were recorded as a thin film on a Nicolet IS5 spectrometer (Thermo Electron Scientific Instruments LLC, Madison, WI, USA). All ¹H and ¹³C-NMR spectra were recorded with a JEOL JMTC-400/54/SS (400 and 100 MHz, respectively) in deuteriochloroform (CDCl₃) containing 0.03% (w/v) of tetramethylsilane as an internal standard. Temperatures shown in schemes or tables were controlled by a constant-temperature oil bath. Yields were determined by ¹H-NMR using 1,1,1,2-tetrachloroethane or 1,1,2,2-tetrachloroethane as an internal standard. Mass spectra were recorded on a JEOL JMS-DS-303 spectrometer (JEOL Ltd., Tokyo, Japan). Flash column chromatography was performed by Yamazen YFLC-AI-580 using Hi-Flash Silica gel 2L Hi-Flash Column 20 mL/min eluted by hexane/EtOAc with the gradation mode changing from 9/1–3/7 depending on R_f values of each compound. Bulb-to-bulb distillation (Kugelrohr) was accomplished at the oven temperature and pressure indicated.
Dehydrated acetonitrile (MeCN) was purchased from commercial sources and used as obtained. Deuterated acetonitrile was also purchased and stored drying over 4 Å molecular sieves. All epoxides, isocyanates, carbodiimide and InCl₃ were also purchased and used as obtained. Bu₂SnI₂ was prepared according to the previous report [74 (link)].

Brominated KA (3) was prepared according to the method by Bertrand et al. (2004) [26 ]. S-cyanoethylthio-dodecaborate (2) was prepared according to the method described previously by Hattori et al. (2011) [27 ]. Flash ODS column chromatography was performed using Isolera Spektra (Biotage Sweden AB, Uppsala, Sweden) with a SNAP KP-C18-HS Cartridge (Biotage Sweden AB, Uppsala, Sweden). ¹H-NMR spectra were measured on a JMTC-400/54/SS (400 MHz, JEOL Ltd., Tokyo, Japan). ESI-MS measurements were performed on an EXACTIVE (Thermo Fisher Scientific, Waltham, MA, USA).