3-Alkenyl-2-silyloxyindoles in Vinylogous Mannich Reactions: Synthesis of Aminated Indole-Based Scaffolds and Products

Autor:	Franca Zanardi, Beatrice Ranieri, Claudio Curti, Giovanni Casiraghi, Gloria Rassu, Lucia Battistini, Giorgio Pelosi, Andrea Sartori
Rok vydání:	2014
Předmět:	Indole test chemistry.chemical_classification Aldimine Indoles Molecular Structure Chemistry Organic Chemistry Stereoisomerism Alkenes Silanes Biochemistry Catalysis Oxindoles chemistry.chemical_compound Organic chemistry Oxindole Lewis acids and bases Physical and Theoretical Chemistry Lewis Acids
Zdroj:	Organic Letters. 16:932-935
ISSN:	1523-7052 1523-7060
DOI:	10.1021/ol4036598
Popis:	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.
Databáze:	OpenAIRE
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