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

被引：64

作者：

Ibrahem, I ^{[1
]}

Córdova, A ^{[1
]}

机构：

[1] Stockholm Univ, Arrhenius Lab, Dept Organ Chem, SE-10691 Stockholm, Sweden

来源：

TETRAHEDRON LETTERS | 2005年 / 46卷 / 16期

关键词：

asymmetric catalysis; proline derivatives; alpha-oxyaldehydes; Mannich reaction; amino sugars;

D O I：

10.1016/j.tetlet.2005.02.116

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first direct amino acid-catalyzed asymmetric syntheses of alpha-oxy-beta-aminoaldehydes are presented. The organocatalytic Mannich reactions between unmodified alpha-oxyaldehydes and anilines proceeded with excellent enantioselectivities. In most cases, the corresponding alpha-oxy-beta-aminoaldehyde adducts were isolated in high yield with excellent chemo- and enantioselectivity. For example, orthogonally protected 3-amino-tetroses and alpha-amino acid derivatives were isolated in up to > 99% ee. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：2839 / 2843

页数：5

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