Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 27, Issue 40, Pages 10349-10355Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.202100355
Keywords
cycloaddition; dihydrobenzofurans; ortho-quinone methides; oxyphosphonium enolates; oxindoles
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Funding
- National Science Foundation [CHE-1665440, 1956170]
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [1956170] Funding Source: National Science Foundation
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An efficient strategy for constructing spirooxindole benzofurans through a (4+1)-cycloaddition was presented, involving an isatin-derived oxyphosphonium enolate. Mechanistic investigations showed a correlation between phosphonium enolate structure and product distribution, which was heavily influenced by solvent and reaction temperature.
An efficient and convergent (4+1)-cycloaddition strategy toward the construction of spirooxindole benzofurans that involves the intermediacy of an isatin-derived oxyphosphonium enolate is presented. Mechanistic investigations employing in situ NMR analysis of the reaction mixture revealed a correlation between phosphonium enolate structure and product distribution that was heavily influenced by the solvent and reaction temperature.
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