Pyrrolidine−Thiourea as a Bifunctional Organocatalyst:  Highly Enantioselective Michael Addition of Cyclohexanone to Nitroolefins

Asymmetric Michael additions of cyclohexanone to both aryl and alkyl nitroolefins in the presence of 20 mol % of organocatalyst 2b and 10 mol % of n-butyric acid afford adducts 5 with high diastereoselectivities and enantioselectivities.

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Bibliographic Details
Published inOrganic letters Vol. 8; no. 14; pp. 2901 - 2904
Main Authors Cao, Chun-Li, Ye, Meng-Chun, Sun, Xiu-Li, Tang, Yong
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 06.07.2006
Amer Chemical Soc
Subjects
Alkenes - chemistry
Catalysis
Chemistry
Chemistry, Organic
Cyclohexanones - chemistry
Molecular Structure
Nitro Compounds - chemistry
Physical Sciences
Pyrrolidines - chemistry
Science & Technology
Stereoisomerism
Thiourea - chemistry
HYDROGEN-BOND DONORS
BETA-NITROSTYRENES
PRACTICAL SYNTHESIS
DIELS-ALDER REACTIONS
MANNICH REACTIONS
ASYMMETRIC STRECKER REACTION
BAYLIS-HILLMAN REACTION
ALDOL REACTIONS
CARBONYL-COMPOUNDS
NITRO-OLEFINS
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Summary:Asymmetric Michael additions of cyclohexanone to both aryl and alkyl nitroolefins in the presence of 20 mol % of organocatalyst 2b and 10 mol % of n-butyric acid afford adducts 5 with high diastereoselectivities and enantioselectivities.
Bibliography:ObjectType-Article-1
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol060481c