OsO4/NaIO4氧化合成醛

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OsO4/NaIO4被称为Lemieux-Johnson试剂,此反应也被称为Lemieux-Johnson氧化。与臭氧化法相比,OsO4/NaIO4是一种温和的烯烃氧化开裂法,在天然产物合成中很有用。烯烃先与OsO4反应生成锇酸酯,再用过碘酸钠氧化,发生开裂,在生成羰基化合物的同时,OsO4再生,所以OsO4用催化量即可。当生成的醛易于分子内缩合时,反应最好在两相系统中进行。


反应实例

 To asolution of 1 (1.8 mg) in THF(1 mL) was added OsO4 (excess) and then a solutionof NaIO4, (excess) in H2O (1 mL). After a period of 1 hr,H2O (5 mL) was added andthe aq. solution was extracted with three 5ml portions of CHCl3.  Thecombined CHCl3 layers were dried over Na2SO4,and concentrated to give a residue, which was separated by preparation TLC (SiO2,5% MeOH-CHCl3). Compounds 2 and 3 were obtained.


Tetrahedron, 41; 6; 1985;1007-1018.



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