Synthesis of enantiopure vicinal diaminoesters and ketopiperazines from N-sulfinylimidazolidines
Synthesis of enantiopure vicinal diaminoesters and ketopiperazines from N-sulfinylimidazolidines
复制标题
DOI：
10.1016/j.tet.2007.05.062
复制
发表时间：
2007-08-13
期刊：
影响因子：
2.1
通讯作者：
Garcia, Ana
中科院分区：
文献类型：
--
作者：
Viso, Alma;de la Pradilla, Roberto Fernandez;Garcia, Ana
介绍了一种含甲氧羰基取代基的单环和双环酮哌嗪的快速高效合成方法。该途径需要对n -亚砜酰咪唑烷进行选择性保护和溶剂分解，从而为邻近的二氨基酯提供适当分化的氮原子。然后，n -酰化/环化方案得到酮哌嗪。此外，本文还描述了一种通过2-哌啶甘氨酸获得天然二酮哌嗪DKP 593A类似物的非对位选择性途径。(C) 2007 Elsevier Ltd.版权所有。
A short and efficient synthesis of mono- and bicyclic ketopiperazines bearing methoxycarbonyl substituents is described. The route entails selective protection and solvolysis of N-sulfinylimidazolidines to provide vicinal diaminoesters with the nitrogen atoms suitably differentiated. Then, an N-acylation/cyclization protocol renders the ketopiperazines. In addition a diastereoselective route to an analog of the natural diketopiperazine DKP 593A through a 2-piperidinylglycinate available by this method is described. (C) 2007 Elsevier Ltd. All rights reserved.