Asymmetric Organocatalytic Double-Conjugate Addition of Malononitrile to Dienones: Efficient Synthesis of Optically Active Cyclohexanones

9-Amino-9-deoxyepiquinine efficiently catalyzed the double-conjugate addition of malononitrile to dienones. A number of 1,1,2,6-tetrasubstituted cyclohexanones were prepared in good yields, diastereoselectivities, and excellent enantioselectivities.

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Bibliographic Details
Published inOrganic letters Vol. 13; no. 3; pp. 374 - 377
Main Authors Li, Xue-ming, Wang, Bo, Zhang, Jun-min, Yan, Ming
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 04.02.2011
Amer Chemical Soc
Subjects
Alkadienes - chemistry
Catalysis
Chemistry
Chemistry, Organic
Cyclohexanones - chemical synthesis
Cyclohexanones - chemistry
Molecular Structure
Nitriles - chemistry
Physical Sciences
Quinolizines - chemistry
Science & Technology
Stereoisomerism
ACTIVATION
STEREOSELECTIVE-SYNTHESIS
ENANTIOSELECTIVE SYNTHESIS
MICHAEL ADDITION
TOOL
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ISSN1523-7060
1523-7052
1523-7052
DOI10.1021/ol102570b

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Summary:9-Amino-9-deoxyepiquinine efficiently catalyzed the double-conjugate addition of malononitrile to dienones. A number of 1,1,2,6-tetrasubstituted cyclohexanones were prepared in good yields, diastereoselectivities, and excellent enantioselectivities.
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ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/ol102570b