Jiang Hao, Nielsen Johanne B, Nielsen Martin, Jørgensen Karl Anker
Danish National Research Foundation: Center for Catalysis, Department of Chemistry, Aarhus University, 8000 Aarhus C, Denmark.
Chemistry. 2007;13(32):9068-75. doi: 10.1002/chem.200700696.
An easy and affordable route for obtaining chiral beta-aminated- and alpha,beta-diaminated aldehydes, 1,3-aminoalcohols, and related compounds by using organocatalysis is presented. The chiral secondary amine (S)-2-[bis(3,5-bistrifluoromethylphenyl)trimethylsilanyloxymethyl]pyrrolidine is used as the catalyst to activate alpha,beta-unsaturated aldehydes, which allows succinimide to add in a 1,4-regio- and stereoselective fashion thereby forming N-protected 1,3-aminoaldehydes in good yields and enantioselectivities. This is followed by two easy transformations giving rise to optically active 1,3-aminoalcohols, a common motif in many biologically active compounds, for example, fibrinogen receptor antagonists. Furthermore, optically active alpha,beta-syn-diaminated aldehydes were obtained by the addition of diethyl azodicarboxylate in a one-pot reaction.
本文介绍了一种通过有机催化获得手性β-氨基化和α,β-二氨基化醛、1,3-氨基醇及相关化合物的简便且经济的方法。手性仲胺（S）-2-[双（3,5-双三氟甲基苯基）三甲基硅烷氧基甲基]吡咯烷用作催化剂来活化α,β-不饱和醛，这使得琥珀酰亚胺能够以1,4-区域和立体选择性方式加成，从而以良好的产率和对映选择性形成N-保护的1,3-氨基醛。接着通过两个简便的转化反应得到具有光学活性的1,3-氨基醇，这是许多生物活性化合物中的常见结构单元，例如纤维蛋白原受体拮抗剂。此外，通过在一锅反应中加入偶氮二羧酸二乙酯获得了具有光学活性的α,β-顺式二氨基醛。
