Enantioselective Construction of Spirooxindole-γ-butyrolactones via NHC-Bound Isobenzofulvene [10π+2π] Cycloaddition

Shuixiu Su; Ying Chen; Qiyu Wang; Jian Zhang; Yang-Zi Liu; Wei-Ping Deng

doi:10.1002/cjoc.70071

Chinese Journal of Chemistry ›› 2025, Vol. 43 ›› Issue (16) : 1983 -1987. DOI: 10.1002/cjoc.70071

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Enantioselective Construction of Spirooxindole-γ-butyrolactones via NHC-Bound Isobenzofulvene [10π+2π] Cycloaddition

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Abstract

We report an N-heterocyclic carbene (NHC)-catalyzed [10π+2π] cycloaddition between indene-2-carbaldehydes and isatins, delivering spirooxindole-γ-butyrolactones with moderate yields (up to 68%) and excellent enantioselectivity (up to 93% ee). This transformation proceeds via NHC-bound isobenzofulvene intermediates and represents the first successful application of all-carbon higherene in NHC-catalyzed [10π+2π] cycloadditions.

Keywords

N-Heterocyclic carbene catalysis / Asymmetric catalysis / Isobenzofulvene / Spiro compounds / Higher-order cycloaddition

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Shuixiu Su, Ying Chen, Qiyu Wang, Jian Zhang, Yang-Zi Liu, Wei-Ping Deng. Enantioselective Construction of Spirooxindole-γ-butyrolactones via NHC-Bound Isobenzofulvene [10π+2π] Cycloaddition. Chinese Journal of Chemistry, 2025, 43(16): 1983-1987 DOI:10.1002/cjoc.70071