The Synthesis Of Chiral Guanidine And Its Application In Asymmetric Michael Addition

In recent years, asymmetric catalyzes reaction is the most prospect method to gain unitary isomerchiral compound, it can gain specially appointed configuration chiral compound with a few chiral catalyzer.Chiral guanidines is one of the main branches of organocatalyst (the other branches being L-proline,cinchona base, chiral phosphoric acid, chiral thiourea and so on), and those who are involved in thesynthesis of chiral molecules consider organocatalyst to be a fundamental tool in their catalysis toolbox.Therefore, synthesis of new chiral guanidines and application of them in enantioselective catalysis havereceived much attention in recent years.In this thesis we focus on the design and synthesis of novel chiral guanidine catalyst. Wesynthesized two series of C2asymmetric chiral guanidine and bicyclic chiral guanidine catalysts under themild and facile conditions. Their application in the asymmetric Michael addition reaction of3-substituted-2-oxindoles and cyclopentenones to enantioselective synthesis of3,3-disubstitutedindolin-3-one derivatives was also studied. Reaction conditions such as solvent, temperature, concentration,catalyst, catalyst loading and additive were optimized. With bicyclic chiral guanidine as catalyst,triethylamine as additives, toluene as solvent, under the condition of-10oC, a series of valuable3,3-disubstituted indolin-3-one derivative were synthesized in high yields (up to99%) and the chiralquaternary-tertiary stereocenters were constructed with excellent enantioselectivity (up to-95%) andstereoselectivities (up to>99:1).