Gold(I)-catalyzed 1,2-acyloxy migration/[3+2] cycloaddition of 1,6-diynes with an ynamide propargyl ester moiety: highly efficient synthesis of functionalized cyclopenta[b]indoles.

Abstract

A gold-catalyzed cycloisomerization of 1,6-diynes containing an ynamide propargyl ester or carbonate moiety has been developed that provides an attractive route to a diverse-substituted 3-acyloxy-1,4-dihydrocyclopenta[b]indoles. Mechanistic studies indicate that the reaction likely proceeds through a competitive 1,2-OAc migration followed by [3+2] cycloaddition of the vinyl gold-carbenoid intermediate with the pendant triple bond. The synthetic utility of the obtained cyclopenta[b]indole products was demonstrated by their efficient transformations by deprotection or double-bond isomerization reactions.