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 in:Organic letters 2007-03, Vol.9 (5), p.923-925
Main Authors: Liu, Kun, Cui, Han-Feng, Nie, Jing, Dong, Ke-Yan, Li, Xiao-Juan, Ma, Jun-An
Format: Article
Language:English
Subjects:
Acetophenones - chemistry
Alkenes - chemistry
Amines - chemistry
Carbohydrates - chemistry
Catalysis
Ketones - chemistry
Molecular Structure
Nitrogen - chemistry
Stereoisomerism
Thiourea - chemical synthesis
Thiourea - chemistry
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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).
ISSN:1523-7060
1523-7052
DOI:10.1021/ol0701666