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A Homodienolate‐Enone Addition
Author(s) -
Bates Robert B.,
Carducci Michael D.,
Kane Vinayak V.,
Lahiri Sanjoy,
Prathap S.,
Singh Vishwakarma K.,
Stessman Chad C.
Publication year - 2000
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200012)2000:23<3823::aid-ejoc3823>3.0.co;2-s
Subject(s) - adduct , chemistry , enone , michael reaction , cyclopropane , protonation , cycloaddition , ketone , methyl vinyl ketone , addition reaction , medicinal chemistry , organic chemistry , ring (chemistry) , catalysis , ion
On treatment with sodium hydride, a mixture of ketone 1 and enone 4 gives a 48% yield of adduct 2 , which contains two new carbon−carbon bonds. The reaction very likely involves homodienolate 3 , which may either undergo a Michael addition or a cycloaddition to enone 4 to give intermediate adduct 6 or 7 , respectively. Adduct 6 may then undergo homo‐Michael addition to give adduct 7 . Cyclopropane ring‐opening of adduct 7 and protonation give the observed adduct 2 .