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

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posted on 2016-10-21, 19:48 authored by Yang Cao, Xiang Zhang, Guangyu Lin, Daisy Zhang-Negrerie, Yunfei Du
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.

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