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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Abstract 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.
AbstractList 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.
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.
Author Lee, Chia-Jui
Chen, Yu-Shan
Chen, Chi-Han
Jang, Yeong-Jiunn
Lin, Wenwei
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CitedBy_id crossref_primary_10_1021_acs_joc_0c01127
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Cites_doi 10.1016/j.ctrv.2009.07.001
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10.1021/ol1029832
10.1016/j.tetlet.2010.11.017
10.1039/b516351j
10.1021/jo902081w
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Issue 1
Keywords Michael addition
diastereoselectivity
cyclohexanone
domino reaction
curcumin
CASCADE REACTIONS
COUMARINS
NITROALKENE
CYCLOADDITION
(-)-EPIBATIDINE
BIFUNCTIONAL THIOUREA
CYCLOHEXANONES
CONSTRUCTION
DERIVATIVES
ALKALOIDS
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Thieme Medical Publishers
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Snippet Abstract The diastereoselective synthesis of 2,6-disubstituted 3-alkanoyl-4-hydroxycyclohex-3-ene-1,1-dicarbonitriles has been developed through domino double...
The diastereoselective synthesis of 2,6-disubstituted 3-alkanoyl-4-hydroxycyclohex-3-ene-1,1-dicarbonitriles has been developed through domino double Michael...
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SubjectTerms Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
Title 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
URI http://dx.doi.org/10.1055/s-0034-1379143
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