Radical Allylation:E-Selective Radical Conjugate Addition-Elimination Reaction from Morita-Baylis-Hillman Adducts

Triethylborane-mediated radical allylation was performed from Morita-Baylis-Hillman alcohols with no need of protecting group. The radical conjugated addition-elimination reaction is highly selective, and trisubstituted E-alkenes were obtained. This reaction opened a new route for the preparation of...

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Bibliographic Details
Published inSynlett Vol. 29; no. 1; pp. 46 - 50
Main Authors Lebargy, Cyril, De Schutter, Coralie, Legay, Remi, Pfund, Emmanuel, Lequeux, Thierry
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 01.01.2018
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
KETONES
radical
ALLYLIC ALCOHOLS
xanthate
CONVERGENT
STEREOSELECTIVE ELIMINATION
alkenes
elimination
allylation
TRICYCLOPOLYPRENOLS
fluorine
enols
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Summary:Triethylborane-mediated radical allylation was performed from Morita-Baylis-Hillman alcohols with no need of protecting group. The radical conjugated addition-elimination reaction is highly selective, and trisubstituted E-alkenes were obtained. This reaction opened a new route for the preparation of functionalized ,-unsaturated ketones.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-0036-1590922