Organocatalytic Michael Addition of Aldehydes to γ-Keto-α,β-unsaturated Esters. An Efficient Entry to Versatile Chiral Building Blocks

The diarylprolinol ether/HOAc-catalyzed Michael addition of aldehydes to γ-keto-α,β-unsaturated esters occurs in a highly regioselective and enantioselective manner. The adducts could easily be converted into synthetically useful cyclohexenones, cyclohexanones, piperidines, and γ-lactones.

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Bibliographic Details
Published in:Organic letters 2008-12, Vol.10 (23), p.5425-5428
Main Authors: Wang, Jing, Ma, Anqi, Ma, Dawei
Format: Article
Language:English
Subjects:
Aldehydes - chemistry
Catalysis
Esters
Ketones - chemistry
Stereoisomerism
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Description
Summary:The diarylprolinol ether/HOAc-catalyzed Michael addition of aldehydes to γ-keto-α,β-unsaturated esters occurs in a highly regioselective and enantioselective manner. The adducts could easily be converted into synthetically useful cyclohexenones, cyclohexanones, piperidines, and γ-lactones.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol802354u