Enantioselective Synthesis of syn/anti-1,3-Amino Alcohols via Proline-Catalyzed Sequential α-Aminoxylation/α-Amination and Horner−Wadsworth−Emmons Olefination of Aldehydes

A novel and general method for asymmetric synthesis of both syn/anti-1,3-amino alcohols is described. The method uses proline-catalyzed sequential α-aminoxylation/ α-amination and Horner−Wadsworth−Emmons (HWE) olefination of aldehydes as the key step. By using this method, a short synthesis of a bio...

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Bibliographic Details
Published inOrganic letters Vol. 12; no. 12; pp. 2762 - 2765
Main Authors Jha, Vishwajeet, Kondekar, Nagendra B, Kumar, Pradeep
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 18.06.2010
Amer Chemical Soc
Subjects
Aldehydes - chemistry
Alkenes - chemistry
Amination
Amino Alcohols - chemical synthesis
Amino Alcohols - chemistry
Catalysis
Chemistry
Chemistry, Organic
Molecular Structure
Physical Sciences
Proline - chemistry
Science & Technology
Stereoisomerism
1,3-AMINO ALCOHOLS
BETA-AMINO KETONES
EFFICIENT APPROACH
REDUCTION
ASYMMETRIC ALDOL REACTIONS
BOND-FORMING REACTIONS
1,3-ASYMMETRIC INDUCTION
ORGANOCATALYSIS
DERIVATIVES
STEREOSELECTIVE SYNTHESIS
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Summary:A novel and general method for asymmetric synthesis of both syn/anti-1,3-amino alcohols is described. The method uses proline-catalyzed sequential α-aminoxylation/ α-amination and Horner−Wadsworth−Emmons (HWE) olefination of aldehydes as the key step. By using this method, a short synthesis of a bioactive molecule, (R)-1-((S)-1-methylpyrrolidin-2-yl)-5-phenylpentan-2-ol, is also accomplished.
Bibliography:ObjectType-Article-1
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol100856u