Base-Catalyzed Domino Double Michael Reactions of 1-Hydroxy-1,4-dien-3-ones and 2-Alkylidenemalononitriles: A Diastereoselective Route to Polysubstituted 3-Alkanoyl-4-hydroxycyclohex-3-enes

Abstract The diastereoselective synthesis of 2,6-disubstituted 3-alkanoyl-4-hydroxycyclohex-3-ene-1,1-dicarbonitriles has been developed through domino double Michael addition of 1,5-disubstituted 1-hydroxy-1,4-dien-3-ones to 2-alkylidenemalononitriles catalyzed by triethylamine. This simple domino...

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Published inSynthesis (Stuttgart) Vol. 47; no. 1; pp. 95 - 107
Main Authors Jang, Yeong-Jiunn, Chen, Yu-Shan, Lee, Chia-Jui, Chen, Chi-Han, Lin, Wenwei
Format Journal Article
LanguageEnglish
Published Stuttgart · New York Georg Thieme Verlag 01.01.2015
Thieme Medical Publishers
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
Michael addition
diastereoselectivity
cyclohexanone
domino reaction
curcumin
CASCADE REACTIONS
COUMARINS
NITROALKENE
CYCLOADDITION
(-)-EPIBATIDINE
BIFUNCTIONAL THIOUREA
CYCLOHEXANONES
CONSTRUCTION
DERIVATIVES
ALKALOIDS
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Summary:Abstract The diastereoselective synthesis of 2,6-disubstituted 3-alkanoyl-4-hydroxycyclohex-3-ene-1,1-dicarbonitriles has been developed through domino double Michael addition of 1,5-disubstituted 1-hydroxy-1,4-dien-3-ones to 2-alkylidenemalononitriles catalyzed by triethylamine. This simple domino process affords a variety of highly functionalized 3-alkanoyl-4-hydroxycyclohex-3-enes, some of which are not easily accessible using other methodologies, in moderate to good yields and excellent diastereoselectivity (dr > 95:5). Thus, the generality of this process and feasibility of introducing bioactive moieties make this reaction highly valuable in synthetic and medicinal chemistry.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-0034-1379143