Unravelling the Nucleophilicity of Butenolides for 1,6-Conjugate Addition to p‑Quinone Methides: A Direct Access to Diversely Substituted Butenolide-Derived Diarylmethanes
A Lewis acid catalyzed regioselective C–C bond is constructed through β-addition of deconjugated butenolides with p-quinone methides in a 1,6-conjugate addition manner. Interestingly, Lewis acid catalyzed vinylogous Mukaiyama–Michael reaction of silyloxyfurans with p-QMs proceeds selectively through...
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Veröffentlicht in: | Organic letters 2018-05, Vol.20 (9), p.2787-2791 |
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Hauptverfasser: | , , , , , , |
Format: | Artikel |
Sprache: | eng |
Online-Zugang: | Volltext |
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Zusammenfassung: | A Lewis acid catalyzed regioselective C–C bond is constructed through β-addition of deconjugated butenolides with p-quinone methides in a 1,6-conjugate addition manner. Interestingly, Lewis acid catalyzed vinylogous Mukaiyama–Michael reaction of silyloxyfurans with p-QMs proceeds selectively through the α or γ position exclusively. The reaction is mild with broad substrate scope, thus allowing easy access to a wide range of bis-arylated α-/β-/γ-substituted butenolides. |
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ISSN: | 1523-7060 1523-7052 |
DOI: | 10.1021/acs.orglett.8b00745 |