Enantioselective Construction of Dihydropyran-Fused Indoles through Chiral Calcium Phosphate Catalyzed Oxo-Hetero-Diels–Alder Reactions by Using 2-Oxoindolin-3-ylidenes as Heterodienes

Authors

  • Zhijie Mao,

    1. School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210093 (China), Fax: (+86) 25-83594886
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  • Weipeng Li,

    1. School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210093 (China), Fax: (+86) 25-83594886
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  • Yan Shi,

    1. School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210093 (China), Fax: (+86) 25-83594886
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  • Haibin Mao,

    1. School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210093 (China), Fax: (+86) 25-83594886
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  • Aijun Lin,

    1. School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210093 (China), Fax: (+86) 25-83594886
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  • Prof. Dr. Chengjian Zhu,

    Corresponding author
    1. School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210093 (China), Fax: (+86) 25-83594886
    2. Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, 200032 (China)
    • School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210093 (China), Fax: (+86) 25-83594886
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  • Prof. Dr. Yixiang Cheng

    Corresponding author
    1. School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210093 (China), Fax: (+86) 25-83594886
    • School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210093 (China), Fax: (+86) 25-83594886
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Abstract

original image

Carbon–carbon bond formation: A highly efficient method for the oxo-hetero-Diels–Alder reaction of 2-oxoindolin-3-ylidenes based on chiral calcium phosphate is described. In general, adducts were obtained with high yields and excellent diastereo- and enantioselectivities (up to 96 % yield, >99:1 endo/exo, >99 % ee; see scheme, Boc=tert-butoxycarbonyl).

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