Highly Enantioselective Michael Addition of Aromatic Ketones to Nitroolefins Promoted by Chiral Bifunctional Primary Amine-thiourea Catalysts Based on Saccharides

A new class of thiourea catalysts have been developed which integrate saccharide and primary amine moieties into one small organic molecule. These simple catalysts are shown to be highly enantioselective for direct Michael addition of aromatic ketones to a range of nitroolefins (up to 98% ee).

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Bibliographic Details
Published inOrganic letters Vol. 9; no. 5; pp. 923 - 925
Main Authors Liu, Kun, Cui, Han-Feng, Nie, Jing, Dong, Ke-Yan, Li, Xiao-Juan, Ma, Jun-An
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 01.03.2007
Amer Chemical Soc
Subjects
Acetophenones - chemistry
Alkenes - chemistry
Amines - chemistry
Carbohydrates - chemistry
Catalysis
Chemistry
Chemistry, Organic
Ketones - chemistry
Molecular Structure
Nitrogen - chemistry
Physical Sciences
Science & Technology
Stereoisomerism
Thiourea - chemical synthesis
Thiourea - chemistry
BETA-NITROSTYRENES
ACTIVATION
DIRECT CONJUGATE ADDITION
STEREOCENTERS
ASYMMETRIC ORGANOCATALYSIS
PYRROLIDINE SULFONAMIDE
DERIVATIVES
QUATERNARY
NITROALKENES
ALPHA,ALPHA-DISUBSTITUTED ALDEHYDES
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Summary:A new class of thiourea catalysts have been developed which integrate saccharide and primary amine moieties into one small organic molecule. These simple catalysts are shown to be highly enantioselective for direct Michael addition of aromatic ketones to a range of nitroolefins (up to 98% ee).
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol0701666