N-Heterocyclic Carbene-Catalyzed Diastereoselective Vinylogous Michael Addition Reaction of γ-Substituted Deconjugated Butenolides.
J Org Chem
; 80(24): 12606-13, 2015 Dec 18.
Article
em En
| MEDLINE
| ID: mdl-26569552
ABSTRACT
An efficient N-heterocyclic carbene (NHC)-catalyzed vinylogous Michael addition of deconjugated butenolides was developed. In the presence of 5 mol % of the NHC catalyst, both γ-alkyl- and aryl-substituted deconjugated butenolides undergo vinylogous Michael addition with various α, ß-unsaturated ketones, esters, or nitriles to afford γ,γ-disubstituted butenolides containing adjacent quaternary and tertiary carbon centers in good to excellent yields with excellent diastereoselectivities. In this process, the free carbene is assumed to act as a strong Brønsted base to promote the conjugate addition.
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01-internacional
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MEDLINE
Idioma:
En
Ano de publicação:
2015
Tipo de documento:
Article