Organocatalytic Enantioselective Epoxidation of Some Aryl-Substituted Vinylidenebisphosphonate Esters: On the Way to Chiral Anti-Osteoporosis Drugs
Organocatalytic Enantioselective Epoxidation of Some Aryl-Substituted Vinylidenebisphosphonate Esters: On the Way to Chiral Anti-Osteoporosis Drugs
复制标题
一些芳基取代的亚乙烯基二膦酸酯的有机催化对映选择性环氧化：通往手性抗骨质疏松药物的道路
DOI：
10.3390/catal7030090
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发表时间：
2017
期刊：
影响因子：
3.9
通讯作者：
G. Strukul
中科院分区：
文献类型：
--
作者：
A. Chiminazzo;L. Sperni;A. Scarso;G. Strukul
报道了以过氧化氢为末端氧化剂，由前手性亚乙烯基二膦酸酯（VBP）前体合成一类新型环氧衍生物的方法。使用一系列可能的具有碱性特征的有机活化剂进行反应，使用奎宁和金雀花碱观察到最好的结果。这些活化剂不仅提供了从良好到优异的环氧化物产率和多种VBPs，而且还提供了在67%-96%ee范围内的令人感兴趣的对映选择性，至少在Ph和m-MeO-Ph VBP衍生物的情况下，为许多手性抗骨质疏松症的潜在活性药物成分开辟了道路。
The synthesis of a new class of epoxide derivatives from prochiral vinylidene bisphosphonate (VBP) precursors is reported using hydrogen peroxide as the terminal oxidant. The reaction is carried out using a series of possible organic activators having a basic character, with the best results being observed using quinine and sparteine. These activators not only provide from good to excellent epoxide yields with a large variety of VBPs, but also interesting enantioselectivities in the 67%–96% ee range, at least in the case of the Ph and m-MeO–Ph VBP derivatives, opening the way to a number of chiral anti-osteoporosis potentially active pharmaceutical ingredients.
影响因子：
4.1
作者：
L. Melton
通讯作者：
L. Melton