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N-Heterocyclic Carbene-Catalyzed [3 + 2] Annulation of 3,3'-Bisoxindoles with α-Bromoenals: Enantioselective Construction of Contiguous Quaternary Stereocenters.

An NHC-catalyzed enantio- and diastereoselective [3 + 2] annulation of α-bromoenals with bisoxindoles is developed, affording efficient access to various spirocyclic bisoxindole alkaloids. This protocol tolerates a broad substrates scope,… Click to show full abstract

An NHC-catalyzed enantio- and diastereoselective [3 + 2] annulation of α-bromoenals with bisoxindoles is developed, affording efficient access to various spirocyclic bisoxindole alkaloids. This protocol tolerates a broad substrates scope, with various spirocyclic bisoxindoles obtained in generally excellent enantioselectivities. More importantly, two contiguous sterically congested all-carbon quaternary stereocenters are successfully created during this process.

Keywords: quaternary stereocenters; catalyzed annulation; annulation; annulation bisoxindoles; carbene catalyzed; heterocyclic carbene

Journal Title: Organic letters
Year Published: 2022

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