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

Binghao Liu, Xiaoyong Duan, Jiahan Li, Yatong Wu, Yanting Li, Jing Qi

Organic Letters · 2022 · 19 citations · 52 references

Concepts

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.

References

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