title: 3-Alkenyl-2-silyloxyindoles in vinylogous Mannich reactions: synthesis of aminated indole-based scaffolds and products.
abstract: The first Lewis acid catalyzed vinylogous Mukaiyama-type Mannich addition of 3-alkenyl-2-silyloxyindoles to in situ generated N-Boc imines has been established, which affords chiral α-alkylidene-δ-amino-2-oxindole products with good efficiency and complete γ-site- and Z-selectivity. The reaction is wide in scope, as it can be applied with equal convenience to different silyloxyindole donors and aromatic or aliphatic aminal-derived aldimine acceptors. The utility of these scaffolds is demonstrated by their easy transformation into either spirocyclopropane oxindole or homotryptamine-like products, featuring nontraditional indole-based skeleton connections.
authors.affiliation: Dipartimento di Farmacia, Università degli Studi di Parma , Parco Area delle Scienze 27A, I-43124 Parma, Italy.
authors.forename: Beatrice
authors.initials: B
authors.lastname: Ranieri
authors.forename: Andrea
authors.initials: A
authors.lastname: Sartori
authors.forename: Claudio
authors.initials: C
authors.lastname: Curti
authors.forename: Lucia
authors.initials: L
authors.lastname: Battistini
authors.forename: Gloria
authors.initials: G
authors.lastname: Rassu
authors.forename: Giorgio
authors.initials: G
authors.lastname: Pelosi
authors.forename: Giovanni
authors.initials: G
authors.lastname: Casiraghi
authors.forename: Franca
authors.initials: F
authors.lastname: Zanardi
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D007211:Indoles / Q000737:chemistry*; D058116:Lewis Acids / Q000737:chemistry*; D015394:Molecular Structure; D000078183:Oxindoles; D012821:Silanes / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D007211:Indoles; D058116:Lewis Acids; D000078183:Oxindoles; D012821:Silanes; C022960:2-oxindole; C030374:indole