Journal
ORGANIC LETTERS
Volume 16, Issue 3, Pages 932-935Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol4036598
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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.
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