Catalytic Enantioselective and Regioselective [3+3] Cycloadditions Using 2‐Indolylmethanols as 3 C Building Blocks |
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Authors: | Xiao‐Xue Sun Hong‐Hao Zhang Guo‐Hao Li Ying‐Ying He Prof?Dr Feng Shi |
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Institution: | Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, School of Chemistry and Chemical Engineering, Jiangsu Normal University, Xuzhou, P. R. China |
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Abstract: | The first catalytic asymmetric cycloaddition using 2‐indolylmethanols as 3C building blocks has been established by a chiral phosphoric acid‐catalyzed enantioselective and regioselective 3+3] cycloaddition of 2‐indolylmethanols with azomethine ylides, which constructed biologically important tetrahydro‐γ‐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. |
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Keywords: | asymmetric catalysis azomethine ylide cycloaddition enantioselectivity organocatalysis |
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