Asymmetric Strecker Reaction Promoted By Amino Acid-derived Multihydrogen-bonding Catalysts

Asymmetric catalysis is an important method to construct chiral drugs and natural products.This dissertation designs and synthesizes a series of hydrogen-bonding catalysts with different skeletons from cheap and commercial L-amino acids.And the method of asymmetric Strecker reactions catalyzed by multihydrogen-bonding catalysts with base was developed.1.The advance in the asymmetric Strecker reactions was introduced from metal catalysis to organocatalysis.Metal catalysis was introduced according to the classification of metal ions.While organocatalysis was introduced according to the classification of catalytic modes.In addition,the applications of hydrogen-bonding catalysts were introduced according to the two catalytic modes,including hydrogen-bonding catalysis and hydrogen-ion-bonding catalysis.2.The asymmetric Strecker reactions of N-Boc/Cbz protected trifluoromethyl ketimines,isatin derived N-Boc ketimines,N-Boc protected acetoacetate imines and N-Boc/Cbz protected aldimines synergistically catalyzed by multihydrogen-bonding catalysts with base have been studied.The catalytic system showed high efficiency,high yields,excellent enantioselectivities and broad substrates scope.Furthermore,the mechanism of the catalytic system was also studied and analyzed by control experiments.In summary,a synergistic catalytic system with both hydrogen-bonding catalyst and base was successfully applied to the asymmetric Strecker reactions of ketoimines and aldimines.The results confirmed the practicability of hydrogen-bonding catalyst and base co-catalyzed asymmetric Strecker reactions.This catalytic system could afford ?-amino nitriles with high efficiency and low catalyst loading.Most important,this method provided a useful routine for constructing the corresponding tertiary or quaternary stereocenters and addressed the limitation of substrates scope catalyzed by hydrogen-bonding catalyst to some extent.The further application of this synergistic catalytic system is undergoing.