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Treatment of α-hetero-substituted cyclic imides with carbonyl compounds mediated by samarium(II) diiodide in the presence of HMPA was found to undergo novel tandem elimination and reductive coupling reactions to generate α-hydroxyalkylated imides in good to high yields. Stereochemistry of the coupling products was researched and the result that increasing the steric bulkiness of the N-substituents...
Samarium(II) diiodide-mediated intramolecular reductive coupling reaction of phthalimides with N-formylated alkyl side chains is shown to afford dihydroxylated tricyclic lactams with 5-7-membered rings. This process was further applied for the preparation of an isoindolobenzazepine alkaloid, chilenine, by featuring the elaboration of the functionalized phthalimide derivative.
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