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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Veröffentlicht in: | Organic letters 2003-05, Vol.5 (10), p.1685-1688 |
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Hauptverfasser: | , , |
Format: | Artikel |
Sprache: | eng |
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Zusammenfassung: | 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. |
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ISSN: | 1523-7060 1523-7052 |
DOI: | 10.1021/ol034333n |