A New Class of Substituted Aryl Bis(oxazoline) Ligands for Highly Enantioselective Copper-Catalyzed Asymmetric Aldol Addition of Dienolsilane to Pyruvate and Glyoxylate Esters

A new class of bis(oxazoline) ligands are introduced that feature o-alkoxyaryl substituents and provide the highest enantioselectivities yet reported for the copper-catalyzed asymmetric dienosilane aldol addition to pyruvate and glyoxylate esters. Enantioselectivities up to 98% ee (before recrystall...

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Bibliographic Details
Published inOrganic letters Vol. 6; no. 22; pp. 4097 - 4099
Main Authors Cong-Dung Le, Julie, Pagenkopf, Brian L
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 28.10.2004
Amer Chemical Soc
Subjects
Aldehydes - chemistry
Catalysis
Chemistry
Chemistry, Organic
Chlorides - chemistry
Copper - chemistry
Esters - chemistry
Glyoxylates - chemistry
Hydrocarbons, Aromatic - chemistry
Ligands
Mesylates - chemistry
Molecular Structure
Oxazoles - chemical synthesis
Physical Sciences
Pyruvates - chemistry
Science & Technology
Silanes - chemistry
Stereoisomerism
CHIRAL LEWIS-ACIDS
KETONES
CYCLOADDITION
DIELS-ALDER REACTIONS
MICHAEL
AZIRIDINATION
COMPLEXES
ALLYLATION
CYCLOPROPANATION
ENOLSILANES
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Summary:A new class of bis(oxazoline) ligands are introduced that feature o-alkoxyaryl substituents and provide the highest enantioselectivities yet reported for the copper-catalyzed asymmetric dienosilane aldol addition to pyruvate and glyoxylate esters. Enantioselectivities up to 98% ee (before recrystallization) and isolated yields up to 91% were observed. Additionally, chloride counterions were found to be superior to triflate for this reaction.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol048179w