Lialh4

Unless otherwise noted, all manipulations are carried
out in either
a nitrogen-filled glovebox or under nitrogen using standard Schlenk
techniques. Reaction solvents were sparged with nitrogen and then
dried by passage through a column of activated alumina using an apparatus
purchased from Anhydrous Engineering. Deuterated benzene and chloroform
and toluene were purchased from Aldrich Chemical Company. Acetone,
benzyl bromide, 1,8-diaminonaphthalene, formic acid, LiAlH₄, MeLi, KN(SiMe₃)₂, triethylorthoformate, and
Pd(OAc)₂ were purchased from Aldrich Chemical Company and
used without further purification. 1-Isopropylperimidine, C₁₀H₆N(ⁱPrN)CH, 1-isopropyl-3-benzylperimidinium
bromide, 2, and 1,3-isopropylperimidine-2-ylidene, 3, were prepared by literature methods.^{22 (link),54 (link)1}H spectra were run on either a Bruker 300, 400,
or
600 MHz spectrometer, and ¹³C{¹H} NMR spectra
were run on either a Bruker 75, 100, or 150 MHz spectrometer using
the residual protons of the deuterated solvent for reference. Elemental
analyses were performed by Midwest Micro lab in Indianapolis, IN,
USA. High-resolution lock mass accuracy mass spectrometry was conducted
on an electrospray global quadrupole time-of-flight spectrometer at
the John L Holmes Mass Spectrometry Facility at the University of
Ottawa.

Reagents and solvents were purchased from several commercial suppliers. TBTU, N,O-dimethylhydroxylamine hydrochloride, TFA, and Cbz-amino acids were obtained from Fluorochem. N-Methyl morpholine were purchased from VWR. TFA, LiAlH₄, methyl (triphenylphosphoranylidene) acetate, and methyl (triphenylphosphoranylidene)-2-propanone were obtained from Merck, as well as silica gel 60 F254 plates and silica gel (200–400 mesh) employed for TLC and column chromatography, respectively. All the TLC were treated with an ethanol solution of phosphomolybdic acid hydrate (15%), which was obtained by Fluorochem, meanwhile, TLC in which aldehydes were evaluated, were treated with 2,4-dinitrophenylhydrazine TLC stain. All the ¹H and ¹³C spectra were performed on a Varian 500 MHz, operating at 499.74 and 125.73 MHz for ¹H and ¹³C, respectively. Deuterated solvents, namely CDCl₃ and MeOD, were obtained from Merck and the signal of the solvents was used as the internal standard. Splitting patterns are described as singlet (s), doublet (d), doublet of doublet (dd), triplet (t), quartet (q), multiplet (m), and broad singlet (bs). Chemical shifts are expressed in ppm and coupling constants (J) in Hz. Elemental analyses were performed on a C. Erba model 1106 (elemental analyzer for C, H, and N) apparatus, and ±0.4% of the theoretical values were found.