Novel efficient synthesis of 1-ethoxyvinyl esters using ruthenium catalysts and their use in acylation of amines and alcohols: synthesis of hydrophilic 3′-N-acylated oxaunomycin derivatives

Novel efficient synthesis of 1-ethoxyvinyl esters using ruthenium catalysts and their use in acylation of amines and alcohols: synthesis of hydrophilic 3′-N-acylated oxaunomycin derivatives
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使用钌催化剂新型有效合成 1-乙氧基乙烯基酯及其在胺和醇酰化中的应用:亲水性 3-N-酰化奥沙诺霉素衍生物的合成

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发表时间:
1993
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影响因子:
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通讯作者:
Y. Tamura
Y. Tamura
中科院分区:
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文献类型:
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作者:
Y. Kita;H. Maeda;Kana Omori;T. Okuno;Y. Tamura

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以羧酸4a-I和乙氧基乙炔5为原料,在催化剂[{RuCl2(对伞花烃)}2]6f的作用下,合成了1-乙氧基乙烯基酯3a-i。这些试剂与胺和醇顺利反应,以极高的产率得到相应的N-和O-酰化化合物。该酰化方法已用于合成亲水性3‘-N-酰化恶青霉素衍生物13a,b。
A novel and efficient synthesis of 1-ethoxyvinyl esters 3a–i from carboxylic acids 4a–i and ethoxyacetylene 5 by using a catalytic amount of ruthenium complex [{RuCl2(p-cymene)}2]6f has been developed. These reagents reacted smoothly with amines and alcohols to give the corresponding N- and O-acylated compounds in excellent yields. This acylation method has been applied to the synthesis of hydrophilic 3′-N-acylated oxaunomycin derivatives 13a, b.