Novel C₂-axis Chiral And Chiralpyrrole-amide Catalysts Were Designed And Synthesized Of Applications In Asymmetric Catalytic Reactions

Organocatalysis has become one of the most active and attractive branch i n asymmetric catalysis since the beginning of this century.Particylary,the near ly last ten years has witnessd an enorous growth concerning new catalyst desig n,new rectiondevelopment and novel catalytic concepts.In this context,asymm etric enamine catalysis and H-bonding catalysis are two of important organocat alytic strategies that hane a substantial impact on this area.Inspired by these f undermental catalytic stategies,we designed a vaitety of multifunctional chiral organocatalysts.Therefore,the higher catalytic activity of chiral pyrrolidine ami de and C₂ axial chiral BINOL amide organocatalysts were designed and synthe sized form commercially available L-proline,and were used in two different as ymmetric catalytic reaction,have achieved good results.1.The asymmetric Michael addition reaction of anthrone to ?-nitrostyrene was catalyzed by novel four kinds of C₂-axis chiral BINOL amide catalysts.Th e optimum conditions for this reaction are the molar ratio of anthrone to nitro olefin is 0.05 mmol: 0.05 mmol and using 15 mmol% of a C₂-axis chiral orga nic small molecule catalyst at room temperature with the presence of 2 mmol of toluene as the solvent.There are twelve enantiomerically riched substituent-n itroanthrone with one chiral centers was synthesized and all compounds were c haracterized by 1H NMR,13 C NMR,IR,and melting point.2.The asymmetric reaction of indole to ?-nitrostyrene was catalyzed by n ovel five kinds of chiral pyrrole amide organic small molecule catalyst.The op timum conditions for this reaction are the molar ratio of indole to nitroolefin i s 0.05 mmol: 0.05 mmol and using 10 mmol% of a pyrrolidine amide-based o rganic small molecule catalyst at room temperature with the presence of 2 m L of dichloromethane as a solvent.There are twelve enantiomerically riched sub stituent-nitroindole with one chiral centers was synthesized and all compounds were characterized by 1H NMR,13 C NMR,IR,and melting point.