Water-Compatible Organocatalysts for Direct Asymmetric syn-Aldol Reactions of Dihydroxyacetone and Aldehydes

A novel organocatalyst was developed that effectively catalyzed the reactions of unprotected or protected dihydroxyacetone with a variety of aldehydes to provide syn-aldol products with good yields and ee values up to >99%. Significantly, this amide catalyst was effective with a variety of nonaro...

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Bibliographic Details
Published inOrganic letters Vol. 10; no. 8; pp. 1621 - 1624
Main Authors Ramasastry, S. S. V, Albertshofer, Klaus, Utsumi, Naoto, Barbas, Carlos F
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 17.04.2008
Amer Chemical Soc
Subjects
Aldehydes - chemistry
Catalysis
Chemistry
Chemistry, Organic
Dihydroxyacetone - chemistry
Physical Sciences
Science & Technology
Water - chemistry
MANNICH REACTION
KETONES
ACID
MICHAEL
DE-NOVO SYNTHESIS
ORGANIC-REACTIONS
NITROOLEFINS
PROLINE
HIGHLY EFFICIENT
ASSEMBLY REACTIONS
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Summary:A novel organocatalyst was developed that effectively catalyzed the reactions of unprotected or protected dihydroxyacetone with a variety of aldehydes to provide syn-aldol products with good yields and ee values up to >99%. Significantly, this amide catalyst was effective with a variety of nonaromatic aldehyde acceptors that had proven difficult in the presence of other catalysts. Reactions of protected dihydroxyacetone proceeded in aqueous media without addition of organic solvents.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol8002833