Expedient asymmetric synthesis of all four isomers of N,N′-protected 2,3-diaminobutanoic acid
Expedient asymmetric synthesis of all four isomers of N,N′-protected 2,3-diaminobutanoic acid
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DOI：
10.1021/jo001152f
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发表时间：
2001-06-15
影响因子：
3.6
通讯作者：
Li, HY
中科院分区：
文献类型：
--
作者：
Robinson, AJ;Stanislawski, P;Li, HY
2，3-二氨基丁酸（DAB）存在于多种肽类抗生素、毒素和生物活性分子中。本文介绍了一种实用的和高对映选择性的合成所有四个N，N '-保护的DAB立体异构体使用的不对称铑（I）-膦催化氢化异构体的烯酰胺作为关键步骤。烯酰胺氢化底物的热和光化学异构化与催化剂-几何异构体配对相结合，允许以最大产率定向合成单一DAB异构体。
2,3-Diaminobutanoic acid (DAB) is found in several peptide antibiotics, toxins, and biologically active molecules. This paper describes the practical and highly enantioselective synthesis of all four N,N'-protected DAB stereoisomers using an asymmetric Rh(I)-phosphine-catalyzed hydrogenation of isomeric enamides as the key step. Thermal and photochemical isomerization of the enamide hydrogenation substrates coupled with catalyst-geometric isomer pairing allows targeted synthesis of single DAB isomers in maximum yield.