Boiling Water Promoted N-Boc Deprotection Reaction And Synthesis/application Of BINOL Based Chiral Phosphorus Acid

This thesis contains two parts.In the first part, we developed a method using boiling water as reaction media to remove Boc protecting group on heterocyclic aromatic amines, aliphatic amines and aromatic amines. In most of the cases, the N-Boc group on the substrate which bearing good solubility in water can be removed effectively in our system. For substrates like di-Boc histamine and di-Boc tryptophan amine, only the Boc group linked to more reactive heterocyclic aromatic amine can be removed, if the reaction was stopped at certain point. We suppose water functions as dual acid/base catalyst in our reaction system. The final decomposition compound of the N-Boc substrate was amine and t-butyl alcohol. Our reaction system is greener than those other reported N-Boc deprotection methods.In the second part, we synthesized several BINOL based chiral phosphorous catalysts bearing various substitute group at 3,3'position and put them into preliminary research on asymmetric catalysis. Our tested asymmetric reactions include:1) F-C reaction between indole and 2,2,2-trifluoro-1-phenylethanone; 2) Michael addition between L-Cystein and (E)-(2-nitrovinyl) benzene; 3) F-C reaction between 3,5-dimethoxyphenol and imine.