Catalytic Enantioselective and Regioselective [3+3] Cycloadditions Using 2-Indolylmethanols as 3C Building Blocks

摘要

The first catalytic asymmetric cycloaddition using 2-indolylmethanols as 3C building blocks has been established by a chiral phosphoric acid-catalyzed enantio-selective and regioselective [3+3] cycloaddition of 2-indolylmethanols with azomethine ylides, which constructed biologically important tetrahydro-gamma-carboline frameworks in high yields and excellent enantioselectivities (up to 83% yield, 99:1 e.r.). 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.