Highly Enantioselective Intermolecular Stetter Reactions of β-Aryl Acceptors: α-Ketoester Moiety as Handle for Activation and Synthetic Manipulations

The use of β,γ-unsaturated-α-ketoesters in the intermolecular Stetter reaction furnishes 1,2,5-tricarbonyl compounds in high yield and excellent enantioselectivity. The α,δ-diketoesters generated using this methodology serve as useful synthetic building blocks via chemo- and diastereoselective trans...

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Bibliographic Details
Published inOrganic letters Vol. 13; no. 18; pp. 4942 - 4945
Main Authors Sánchez-Larios, Eduardo, Thai, Karen, Bilodeau, François, Gravel, Michel
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 16.09.2011
Amer Chemical Soc
Subjects
Aldehydes - chemical synthesis
Aldehydes - chemistry
Chemistry
Chemistry, Organic
Esters - chemistry
Ketones - chemical synthesis
Ketones - chemistry
Molecular Structure
Physical Sciences
Science & Technology
Stereoisomerism
N-HETEROCYCLIC CARBENE
ACYLATION
SCOPE
DOUBLE-BONDS
ORGANOCATALYSIS
ALDEHYDES
FLUORINATION
CATALYST
SALTS
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Summary:The use of β,γ-unsaturated-α-ketoesters in the intermolecular Stetter reaction furnishes 1,2,5-tricarbonyl compounds in high yield and excellent enantioselectivity. The α,δ-diketoesters generated using this methodology serve as useful synthetic building blocks via chemo- and diastereoselective transformations.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/ol202040b