A simplified route to (E)-2-alkylidene-1,4-diketones

Conjugate addition of nitroalkanes to allyl Baylis-Hillman acetates 1 in the presence of NaOH (0.6 N) in THF gave 2-alkylidene-4-nitro ketones 2 with total stereoselectivity, which were further converted via the Nef reaction into the corresponding 1,4-diketones 3 in fair to good yields.

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Bibliographic Details
Published inSynthesis (Stuttgart) no. 2; pp. 295 - 299
Main Authors Chamakh, A, M'hirsi, M, Villieras, J, Lebreton, J, Amri, H
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 2000
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
MICHAEL REACTION
CARBONYLS
SUBSTITUTION
Baylis-Hillman products
CONVERSION
addition reactions
Nef reaction
2-alkylidene-1,4-diketones
cyclizations
ETHERS
NITRO-COMPOUNDS
ESTERS
NITROALKANES
ACETATES
DERIVATIVES
tandem reactions
hydrolysis
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Summary:Conjugate addition of nitroalkanes to allyl Baylis-Hillman acetates 1 in the presence of NaOH (0.6 N) in THF gave 2-alkylidene-4-nitro ketones 2 with total stereoselectivity, which were further converted via the Nef reaction into the corresponding 1,4-diketones 3 in fair to good yields.
ISSN:0039-7881
DOI:10.1055/s-2000-6257