Amino acid catalyzed direct enantioselective formation of carbohydrates:: one-step de novo synthesis of ketoses

被引：118

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 / 19期

关键词：

asymmetric synthesis; amino acids; carbohydrates; catalysis; biomimetic;

D O I：

10.1016/j.tetlet.2005.03.084

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The amino acid-catalyzed direct enantioselective one-step de novo synthesis of carbohydrates using dihydroxyacetone phosphate mimetics as donors and aldehydes or in situ generated imines as acceptors is presented. The addition of water significantly accelerates as well as improves the enantioselectivity of the biomimetic aldol and Mannich reactions. The C-3+C-n methodology presented herein is a direct entry to orthogonally protected C-5 and C-6 ketoses (e.g., ribulose, tagatose and piscose) and deoxy- and aminosugars such as 4-amino-4-deoxy-fructose. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：3363 / 3367

页数：5

共 83 条

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