Organocatalytic Asymmetric Assembly Reactions:  One-Pot Synthesis of Functionalized β-Amino Alcohols from Aldehydes, Ketones, and Azodicarboxylates

l-Proline catalyzed the enzyme-like direct asymmetric assembly of aldehydes, ketones, and azodicarboxylic acid esters to provide optically active β-amino alcohols. This assembly reaction uses both aldehydes and ketones as donors in one pot. The aldol-derived stereocenter is formed with a reduced fac...

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Bibliographic Details
Published in:Organic letters 2003-05, Vol.5 (10), p.1685-1688
Main Authors: Chowdari, Naidu S, Ramachary, D. B, Barbas, Carlos F
Format: Article
Language:English
Subjects:
Aldehydes - chemistry
Amino Alcohols - chemical synthesis
Aza Compounds - chemical synthesis
Aza Compounds - chemistry
Catalysis
Dicarboxylic Acids - chemical synthesis
Dicarboxylic Acids - chemistry
Ketones - chemistry
Models, Molecular
Molecular Conformation
Proline - chemistry
Solvents
Stereoisomerism
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Summary:l-Proline catalyzed the enzyme-like direct asymmetric assembly of aldehydes, ketones, and azodicarboxylic acid esters to provide optically active β-amino alcohols. This assembly reaction uses both aldehydes and ketones as donors in one pot. The aldol-derived stereocenter is formed with a reduced facial selectivity in reactions involving (R)-amino aldehydes. The reactions can be performed on a multigram scale under operationally simple and safe conditions without the requirement of an inert atmosphere or dry solvents.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol034333n