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ChemInform Abstract: The Vinyl Moiety as a Handle for Regiocontrol in the Preparation of Unsymmetrical 2,3-Aliphatic-Substituted Indoles and Pyrroles.

✍ Scribed by Malcolm P. Huestis; Lina Chan; David R. Stuart; Keith Fagnou

Publisher: John Wiley and Sons
Year: 2011
Weight: 51 KB
Volume: 42
Category: Article
ISSN: 0931-7597
DOI: 10.1002/chin.201121112

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✦ Synopsis

The Vinyl Moiety as a Handle for Regiocontrol in the Preparation of Unsymmetrical 2,3-Aliphatic-Substituted Indoles and Pyrroles. -Rh-catalyzed reactions of anilides (I) or methyl-2-acetamidoacrylate (VI) with various enynes proceed with excellent regioselectivity to furnish 2-alkenyl indoles and pyrroles, respectively. The functionalized enyne (VIII) allows the synthesis of a C-3 unsubstituted pyrrole after removal of the silyl group from (IX). Furthermore, hydrogenations of the unsaturated side chains and removal of the -Mac protecting group are presented. -(HUESTIS*,

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