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.

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页码：4226 / 4232

页数：7

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