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      Highly enantioselective construction of spiro[4H-pyran-3,3'-oxindoles] through a domino Knoevenagel/Michael/cyclization sequence catalyzed by cupreine.

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          Abstract

          The first enantioselective organocatalytic two- and three-component reactions via a domino Knoevenagel/Michael/cyclization sequence with cupreine as catalyst have been developed. A wide range of optically active spiro[4H-pyran-3,3'-oxindoles] were obtained in excellent yields (up to 99%) with good to excellent enantioselectivities (up to 97%) from simple and readily available starting materials under mild reaction conditions. These heterocyclic spirooxindoles will provide promising candidates for chemical biology and drug discovery.

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          Author and article information

          Journal
          Org. Lett.
          Organic letters
          American Chemical Society (ACS)
          1523-7052
          1523-7052
          Jul 16 2010
          : 12
          : 14
          Affiliations
          [1 ] Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, China.
          Article
          10.1021/ol1009224
          20545337
          801c0185-2ce6-476b-a771-1098fd084bad
          History

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