Highly diastereo- and enantioselective direct aldol reactions promoted by water-compatible organocatalysts bearing a pyrrolidinyl-camphor structural scaffold

Zheng Hao Tzeng, Hung Yao Chen, Raju Jannapu Reddy, Ching Ting Huang, Kwunmin Chen

    研究成果: 雜誌貢獻文章同行評審

    58 引文 斯高帕斯(Scopus)

    摘要

    Efficient synthetic routes have been developed for the synthesis of a series of pyrrolidinyl-camphor containing organocatalysts (1-10). Structural modifications were made by varying the stereo- and electronic properties of the camphor scaffold and the aromatic substituents. These readily tunable and amphiphilic organocatalysts were evaluated for the direct asymmetric aldol reaction of various aromatic aldehydes and cyclohexanone either in organic solvents or in the presence of water. The aldol reaction proceeded smoothly with excellent chemical yields (up to 99%), enantioselectivities (up to 99% ee), and anti-diastereoselectivities (up to 99:1) with a catalytical amount of the bifunctional organocatalysts (20 mol %) under optimal reaction conditions. Mechanistic transition models are proposed and the stereochemical bias of the asymmetric aldol reaction is presented.

    原文英語
    頁(從 - 到)2879-2888
    頁數10
    期刊Tetrahedron
    65
    發行號15
    DOIs
    出版狀態已發佈 - 2009 四月 11

    ASJC Scopus subject areas

    • Biochemistry
    • Drug Discovery
    • Organic Chemistry

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