Palladium-catalyzed synthesis of carcinogenic polycyclic aromatic hydrocarbon epoxide-nucleoside adducts: the first amination of a chloro nucleoside.
Palladium-catalyzed synthesis of carcinogenic polycyclic aromatic hydrocarbon epoxide-nucleoside adducts: the first amination of a chloro nucleoside.
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钯催化合成致癌多环芳烃环氧化物-核苷加合物：氯核苷的第一次胺化。
DOI：
10.1021/ol027084w
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发表时间：
2003
期刊：
影响因子：
5.2
通讯作者：
Gunda,Padmaja
中科院分区：
文献类型：
--
作者：
Lakshman,MaheshK;Gunda,Padmaja
钯催化偶联的轴向约束，反应性较低的苯并[a]芘bay-region氨基苯甲酸酯，衍生自四氢和二醇环氧化物，与C-6和C-2卤嘌呤脱氧核苷提供了一种有效的方法来合成相应的核苷环氧加合物。还报道了涉及6-氯嘌呤脱氧核苷与这些胺的偶联的第一个实例，该反应通过直接卤化物置换是困难的。这种金属催化的C-N键形成的某些机制方面也进行了讨论。
Pd-catalyzed coupling of the axially constrained, less reactive benzo[a]pyrene bay-region amino benzoates, derived from the tetrahydro and diol epoxides, with C-6 and C-2 halopurine deoxynucleosides offers an efficient approach to the synthesis of the corresponding nucleoside−epoxide adducts. Also reported are the first examples involving the coupling of a 6-chloropurine deoxynucleoside with these amines, a reaction that is difficult by direct halide displacement. Certain mechanistic aspects of this metal-catalyzed C−N bond formation are also discussed.