We have established a substrate-controlled [3+2] cycloaddition and vinylation of γ-allenoates with α,α-dicyanoolefins in the presence of phosphine.Indole-incorporated highly functionalized cyclopentenes can be synthesized in good yields(up to 97%yield).N-functionalization of indole-derived α,α-dicyanoolefins could also be realized by using nitrogen free indole-derived α,α-dicyanoolefin in the presence of phosphine.In sharp contrast to cyclopentenes obtained in previous studies of phosphine catalyzed [3+2] cycloaddition of γ-allenoates with α,α-dicyanoolefin,carbon-carbon double bond shifts in cyclopentene obtained in this study by using γ-aromatic allenoates.1,2