Construction of Spiropyrroloindolines by Dearomative [3+2]-Cycloaddition of Indoles with Oxindole-Embedded Azaoxyallyl ­Cations

A dearomative [3+2]-cycloaddition reaction of oxindole-embedded azaoxyallyl cations with indoles at the C3 position has been developed. The use of this new class of azaoxyallyl cation species in the reaction permits access to more-elaborate hexahydropyrrolo[2,3-b]indole moieties that contain a spiro-oxindole ring. The transformation displays a broad substrate scope and good regio- and stereoselectivity for the cycloaddition step. Several observations suggested that this class of azaoxyallyl cations can display a different reactivity pattern from those of commonly employed azaoxyallyl cation systems.