Highly enantioselective epoxidation of α,β-unsaturated esters by chiral dioxirane

Highly enantioselective epoxidation of α,β-unsaturated esters by chiral dioxirane
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DOI:
10.1021/ja020478y
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发表时间:
2002-07-31
影响因子:
15
通讯作者:
Shi, YA
Shi, YA
中科院分区:
化学1区
文献类型:
--
作者:
Wu, XY;She, XG;Shi, YA

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以果糖衍生的酮2为催化剂,过硫酸氢钾为氧化剂,对α,β-不饱和酯进行了高对映选择性的环氧化反应。许多反式和三取代的底物都获得了高ee值(82−98% ee)。结果表明,双环氧乙烷能有效地环氧化高ee值的缺电子烯烃。
This paper describes a highly enantioselective epoxidation of α,β-unsaturated esters using the fructose-derived ketone2as catalyst and Oxone as oxidant. High ee's have been obtained for a number of trans and trisubstituted substrates (82−98% ee). The results described show that it is feasible for dioxiranes to effectively epoxidize electron-deficient olefins with high ee's.