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Metalloporphyrin-catalyzed diastereoselective epoxidation of allyl-substituted alkenes

被引：18
作者：
Chan, WK
Wong, MK
Che, CM
机构：
[1] Univ Hong Kong, Dept Chem, Inst Mol Technol Drug Discovery & Synth, Hong Kong, Hong Kong, Peoples R China
[2] Univ Hong Kong, Dept Chem, Open Lab Chem Biol, Hong Kong, Hong Kong, Peoples R China
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 70卷 / 11期
关键词：
D O I：
10.1021/jo047733c
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
By using [Mn(2,6-Cl2TPP)Cl] (1) as a catalyst and Oxone/H2O2 as an oxidant, we have developed an efficient method for erythro-selective epoxidation of acyclic allyl-substituted alkenes, including allylic alcohols, amines, and esters. Up to 9:1 erythro selectivities for terminal allyllic alkenes could be achieved, which are significantly higher than that achieved using m-CPBA as an oxidant. In addition, the synthetic utilities of this epoxidation method were highlighted in stereoselective synthesis of key anti-HIV drug intermediates and epoxidation of glycals.
引用
收藏
页码：4226 / 4232
页数：7
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