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

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 alpha-alkylidene-delta-amino-2-oxindole products with good efficiency and complete gamma-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.