Study On Synthesis Of Novel Spirooxindol-2,3-Dihydrofuran Compounds And Asymmetric Transfer Hydrogenation Of N-(1-Arylethenyl) Acetamide

This dissertation consists of two parts:The first part was study on a series of novel spirooxindol-2,3-dihydrofuran chiral compounds were synthesized in the presence of cinchonine. The second part was study on asymmetric transfer hydrogenation of N-(1-arylethenyl)acetamide catalyzed by chiral (R)-BINAP/Ir(I) systemsPart1:The indole and dihydrofuran represent the core structure of large numbers important natural products and biologically active compounds. Asymmetric [3+2] cycloaddition of isatin derivatives (3-hydroxy-l-methylindolin-2-one) with cinnamonitrile derivatives by employing a commercially available, low cost cinchonine as the organocatalyst was developed. A series of optically active and novel spirooxindol-2,3-dihydrofuran compounds were obtained in high yields (90%-99%), with moderate diastereoselectivities (54:46-91:9) enantioselectivities (up to84%ee).Part2:Hydrogen transfer reaction is more secure than hydrogenation with hydrogen source. So hydrogen transfer reaction is widely applicable both in laboratory research and industrial production. The chiral (-R)-BINAP-Ir(I) complexs were effective catalyst for asymmetric transfer hydrogenation of various N-acetylenamides to give acetamide in high conversion (up to100%) and moderate enantioselectivity (up to72%ee) at100℃in2-propanol.