6006-15-1Relevant academic research and scientific papers
Reductive amination of ketones/aldehydes with amines using BH3N(C2H5)3as a reductant
Zou, Qizhuang,Liu, Fei,Zhao, Tianxiang,Hu, Xingbang
supporting information, p. 8588 - 8591 (2021/09/04)
Herein, we report the first example of efficient reductive amination of ketones/aldehydes with amines using BH3N(C2H5)3 as a catalyst and a reductant under mild conditions, affording various tertiary and secondary amines in excellent yields. A mechanistic study indicates that BH3N(C2H5)3 plays a dual function role of promoting imine and iminium formation and serving as a reductant in reductive amination. This journal is
Stereodynamics of 2-(diethylamino)propane and 2-(dibenzylamino)propane. 1H and 13C{1H} DNMR studies. Molecular mechanics calculations
Brown, Jay H.,Bushweller, C. Hackett
, p. 12567 - 12577 (2007/10/03)
2-(Diethylamino)propane (DEAP) and 2-(dibenzylamino)propane (DBAP) possess similar molecular symmetries. Interconversion among the stable equilibrium conformations occurs by inversion-rotation at the pyramidal nitrogen and by isolated rotation about carbon-nitrogen bonds. In DEAP and DBAP, the fact that stable equilibrium conformations cannot have destabilizing syn-1,5 interactions between methyl or phenyl groups limits the number of equilibrium conformations that will be present at concentrations high enough to be NMR detectable. The 1H and 13C{1H} NMR spectra of DEAP at 100 K show two diastereomeric pairs of enantiomeric conformations. One pair of enantiomers has the isopropyl methine proton and both ethyl methyl groups gauche to the lone pair (75%). The other pair has the methine proton anti to the lone pair with the ethyl methyl groups respectively gauche and anti to the lone pair (25%). The barrier to inversion-rotation in DEAP (ΔG? = 6.4 kcal/mol) is higher than barriers to isolated rotation about carbon-nitrogen bonds (ΔG? = 5.3-5.7 kcal/mol). The 1H and 13C{1H} NMR spectra of DBAP at 100 K show just one pair of enantiomeric conformations that have the isopropyl methine proton and both phenyl groups gauche to the lone pair. There is no evidence in the NMR spectrum at 100 K for those conformations of DBAP that have a phenyl group anti to the lone pair. The barrier to inversion-rotation in DBAP (ΔG? = 6.4 kcal/mol) is higher than the barrier to racemization via isolated rotation about carbon-nitrogen bonds (ΔG? = 5.5 kcal/mol). Molecular mechanics calculations of conformational energies are in good agreement with the observed conformational preferences.
Enolboration. 5. An Examination of the Effects of Amine, Solvent, and Other Reaction Parameters on the Stereoselective Enolboration of Ketones with Various Chx2BX Reagents. An Optimized Procedure To Achieve the Stereoselective Synthesis of E Enol Borinate
Ganesan, Kumeraperumal,Brown, Herbert C.
, p. 7162 - 7169 (2007/10/02)
The effects of amine, solvent, concentration, temperature and other reaction parameters in controlling the enolate geometry have been systematically investigated in the present study.A 11B NMR study of the interaction of representative tertiary amines of
