REACTIONS OF 2-VINYLINDOLES WITH CARBODIENOPHILES - SYNTHETIC AND MECHANISTIC ASPECTS

Reactions of selectively functionalized 2-vinylindoles with acyclic and cyclic carbodienophiles proceed with high regio- and/or stereoselectivities to furnish Diels-Alder adducts, Diels-Alder ene products, and Michael adducts. This methodology provides a convenient route to functionalized indoles, carbazoles, and [c]pyrrolo-annelated carbazoles with substitution patterns that are not easily obtained by the usual routes. Some mechanistic aspects of the chemistry of 2-vinylindoles are discussed. © 1990 American Chemical Society.