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

Chowdari, Naidu S. ; Ramachary, D. B. ; Barbas, Carlos F. (2003) Organocatalytic Asymmetric Assembly Reactions: One-Pot Synthesis of Functionalizedβ-Amino Alcohols from Aldehydes, Ketones, and Azodicarboxylates Organic Letters, 5 (10). pp. 1685-1688. ISSN 1523-7060

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Official URL: http://doi.org/10.1021/ol034333n

Related URL: http://dx.doi.org/10.1021/ol034333n

Abstract

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.

Item Type:Article
Source:Copyright of this article belongs to American Chemical Society.
ID Code:120794
Deposited On:05 Jul 2021 11:34
Last Modified:05 Jul 2021 11:34

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