Amino acid-catalyzed direct enantioselective synthesis of β-amino-α-oxyaldehydes |
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Authors: | Ismail Ibrahem |
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Institution: | Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, SE-106 91 Stockholm, Sweden |
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Abstract: | 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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Keywords: | Asymmetric catalysis Proline derivatives α-Oxyaldehydes Mannich reaction Amino sugars |
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