Chiral Phosphoric Acid-Catalyzed Asymmetric Reactions Involving Indolylmethanols And Vinylindoles

In the first chapter,we introduced the background on chiral phosphoric acid(CPA)catalyzed asymmetric reactions involving indolylmethanols and vinylindoles.Besides,the goal and the contents of this dissertation were also introduced.In the second chapter,we established the catalytic enantioselective arylation of 3-indolylmethanols in an atom economic fashion,which efficiently assembles isatin-derived 3-indolylmethanols and 3-methylindoles into biologically important 3,3'-bisindolyl oxindoles bearing a quaternary stereogenic center in high yields and good enantioselectivities.In the third chapter,we established the catalytic asymmetric cycloaddition using 2-indolylmethanols as 3C building blocks,which makes use of chiral phosphoric acid-catalyzed enantioselective and regioselective [3+3] cycloaddition of 2-indolylmethanols with azomethine ylides,leading to the construction of biologically important tetrahydro-?-carboline framework at high yields and excellent enantioselectivities.This reaction not only represents the first application of 2-indolylmethanols as 3C building blocks in catalytic asymmetric cycloadditions,but also has established an abnormal regioselectivity in indolylmethanol-involved transformations.More importantly,this approach has settled the great challenges in 2-indolylmethanol-involved catalytic asymmetric cycloadditions,which will open a new window for developing 2-indolylmethanol-involved catalytic enantioselective transformations.In the fourth chapter,we established the catalytic asymmetric [3+2] cyclization of quinone monoimides(QMI)with olefins,which employed 3-vinylindoles as a class of competent olefins and spiro-CPA as a powerful chiral catalyst,leading to chemo-,diastereo-and enantioselective construction of biologically important 2,3-dihydrobenzofuran framework with optical purity.This reaction not only served as a good example of applying QMI in asymmetric catalysis for synthesizing enantioenriched oxygenous heterocycles,but also provided an efficient organocatalytic strategy for constructing enantioenriched 2,3-dihydrobenzofuran frameworks which frequently occurred in natural products.