Organocatalytic formal [5+1] annulation: diastereoselective cascade synthesis of functionalized six-membered spirocyclic indane-1,3-diones/oxindoles via Michael–aldol reaction |
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Authors: | Suparna Roy Mamatha AmireddyKwunmin Chen |
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Institution: | Chemistry Department, National Taiwan Normal University, 88 Sec. 4, TingChow Rd., Taipei 116, Taiwan |
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Abstract: | An efficient cascade protocol has been developed for the diastereoselective synthesis of functionalized six-membered spirocyclic compounds. The reaction proceeded smoothly between indane 1,3-diones/oxindoles/coumaranone as the dinucleophilic components and (E)-5-nitro-6-aryl-hex-5-en-2-one as the dielectrophile to give the desired products with reasonable to high chemical yields (30–84%) and high levels of diastereoselectivities (upto >95:5 dr). The reaction proceeded smoothly via cascade Michael–aldol reaction. |
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Keywords: | Cascade Michael&ndash aldol Oxindole Diastereoselectivity |
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