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, with various spirocyclic bisoxindoles obtained in generally e...

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Bibliographic Details
Published in:Organic letters 2022-08, Vol.24 (32), p.5929-5934
Main Authors: Liu, Binghao, Duan, Xiao-Yong, Li, Jiahan, Wu, Yatong, Li, Yanting, Qi, Jing
Format: Article
Language:English
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.2c02180