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  • Title: 1,4-Diazepinone and pyrrolodiazepinone syntheses via homoallylic ketones from cascade addition of vinyl Grignard reagent to alpha-aminoacyl-beta-amino esters.
    Author: Iden HS, Lubell WD.
    Journal: Org Lett; 2006 Aug 03; 8(16):3425-8. PubMed ID: 16869626.
    Abstract:
    [reaction: see text] 1,4-Diazepinones 5 and pyrrolodiazepinones 8 and 9 were synthesized from common homoallylic ketone precursors 4 prepared by copper-catalyzed cascade addition of a vinyl Grignard reagent to alpha-aminoacyl beta-amino esters 3. Nitrogen deprotection and intramolecular reductive amination yielded 1,4-diazepinones 5. Olefin oxidation, Boc removal, and intramolecular Paal-Knorr condensation gave pyrrolodiazepinones 8 and 9. X-ray structures of diazepinones 5c and 5d depicted dihedral angles about the alpha-amino acid moiety similar to those of the central residue in an ideal reverse gamma-turn.
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