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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.