Amino acid-catalyzed direct enantioselective synthesis of β-amino-α-oxyaldehydes

Ismail Ibrahem; Armando Córdova

doi:10.1016/j.tetlet.2005.02.116

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Amino acid-catalyzed direct enantioselective synthesis of β-amino-α-oxyaldehydes

Journal article

Peer reviewed

Amino acid-catalyzed direct enantioselective synthesis of β-amino-α-oxyaldehydes

Ismail Ibrahem and Armando Córdova

Tetrahedron letters, Vol.46(16), pp.2839-2843

18/04/2005

DOI: https://doi.org/10.1016/j.tetlet.2005.02.116

Abstract

Amino sugars

Asymmetric catalysis

Mannich reaction

Proline derivatives

α-Oxyaldehydes

[Display omitted] The first direct amino acid-catalyzed asymmetric syntheses of α-oxy-β-aminoaldehydes are presented. The organocatalytic Mannich reactions between unmodified α-oxyaldehydes and anilines proceeded with excellent enantioselectivities. In most cases, the corresponding α-oxy-β-aminoaldehyde adducts were isolated in high yield with excellent chemo- and enantioselectivity. For example, orthogonally protected 3-amino-tetroses and α-amino acid derivatives were isolated in up to >99% ee.

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Title: Amino acid-catalyzed direct enantioselective synthesis of β-amino-α-oxyaldehydes
Creators - without role: Ismail Ibrahem - Stockholm University
Armando Córdova - Stockholm University
Publication Details: Tetrahedron letters, Vol.46(16), pp.2839-2843
Publisher: Elsevier Ltd
Identifiers: 9912098008331
Academic Unit: Al Baha University
Language: English
Resource Type: Journal article