Metal‐Free Rearrangement of Spirofurooxindoles into Spiropentenoneoxindoles and Indoles: Implications for the Mechanism and Stereochemistry of the Piancatelli Rearrangement | Zendy

Yin Biaolin | Zendy; Huang Li | Zendy; Wang Xiujun | Zendy; Liu Jianchao | Zendy; Jiang Huanfeng | Zendy

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Metal‐Free Rearrangement of Spirofurooxindoles into Spiropentenoneoxindoles and Indoles: Implications for the Mechanism and Stereochemistry of the Piancatelli Rearrangement

Author(s) -

Yin Biaolin,

Huang Li,

Wang Xiujun,

Liu Jianchao,

Jiang Huanfeng

Publication year - 2013

Publication title -

advanced synthesis and catalysis

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.541

H-Index - 155

eISSN - 1615-4169

pISSN - 1615-4150

DOI - 10.1002/adsc.201200850

Subject(s) - chemistry , cope rearrangement , mechanism (biology) , carroll rearrangement , rearrangement reaction , stereochemistry , sigmatropic reaction , organic chemistry , catalysis , philosophy , epistemology

Spirofurooxindoles derived from α‐furylcarbinols were rearranged into spirocyclopentenoneoxindoles exclusively or as a mixture of spirocyclopentenoneoxindoles and indoles under different reaction conditions. Along with our previous studies, the stepwise C ‐Piancatelli rearrangement has been presented for the first time.

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