title: Benzannulation via the reaction of ynamides and vinylketenes. application to the synthesis of highly substituted indoles.
abstract: A two-stage "tandem strategy" for the synthesis of indoles with a high level of substitution on the six-membered ring is described. Benzannulation based on the reaction of cyclobutenones with ynamides proceeds via a cascade of four pericyclic reactions to produce multiply substituted aniline derivatives in which the position ortho to the nitrogen can bear a wide range of functionalized substituents. In the second stage of the tandem strategy, highly substituted indoles are generated via acid-, base-, and palladium-catalyzed cyclization and annulation processes.
authors: Department of Chemistry, Massachusetts Institute of Technology , Cambridge, Massachusetts 02139, United States.
authors: Tin Yiu
authors: TY
authors: Lam
authors: Yu-Pu
authors: YP
authors: Wang
authors: Rick L
authors: RL
authors: Danheiser
mesh_terms: D000577:Amides / Q000737:chemistry*; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D014753:Vinyl Compounds / Q000737:chemistry*
chemical_list: D000577:Amides; D007211:Indoles; D007659:Ketones; D014753:Vinyl Compounds
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