Enantioselective synthesis of (-)-chloramphenicol via silver-catalysed asymmetric isocyanoacetate aldol reaction.
Enantioselective synthesis of (-)-chloramphenicol via silver-catalysed asymmetric isocyanoacetate aldol reaction.
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DOI：
10.1039/c5ob02141c
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发表时间：
2016-01-07
影响因子：
3.2
通讯作者：
Dixon DJ
中科院分区：
文献类型：
--
作者：
Franchino A;Jakubec P;Dixon DJ
报道了一种利用对硝基苯甲醛和异氰乙酸二苯甲酯催化的不对称羟醛缩合反应合成（-）-氯霉素的简便方法。本文报道了Ag_2O和金鸡纳衍生的氨基膦催化异氰乙酸酯的高对映选择性和非对映选择性的Aldol反应，并将其应用于（-）-和（+）-氯霉素的合成。简洁的合成展示了这种催化不对称方法用于制备具有α-氨基-β-羟基基序的生物活性化合物的实用性。
A concise synthesis of (–)-chloramphenicol, based on the catalytic asymmetric aldol reaction between 4-nitrobenzaldehyde and benzhydryl isocyanoacetate, is reported. The highly enantio- and diastereoselective aldol reaction of isocyanoacetates catalysed by Ag2O and cinchona-derived amino phosphines applied to the synthesis of (–)- and (+)-chloramphenicol is described. The concise synthesis showcases the utility of this catalytic asymmetric methodology for the preparation of bioactive compounds possessing α-amino-β-hydroxy motifs.