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
Hauptverfasser: Sharma, Brijesh M, Shinde, Dinesh R, Jain, Ruchi, Begari, Eeshwaraiah, Satbhaiya, Shruti, Gonnade, Rajesh G, Kumar, Pradeep
Format: Artikel
Sprache:eng
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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.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.8b00745