Chiral Aryliodine-Mediated Enantioselective Organocatalytic Spirocyclization: Synthesis of Spirofurooxindoles via Cascade Oxidative C–O and C–C Bond Formation

An
enantioselective organocatalytic oxidative spirocyclization
of alkyl 3-oxopentanedioate monoamide derivatives leading to the formation
of diverse spirofurooxindoles with high enantioselectivity has been
realized via chiral aryliodine-mediated cascade C–O and C–C
bond formations. The reaction is postulated to proceed via oxidative
C–O bond formation followed by oxidative C–C bond formation,
with the latter being the enantioselectivity-determining step.