由有机卤化锌试剂合成二氢茉莉酮酸甲酯的新方法

Synthesis of methyl dihydrojasmonate from organozinc halide

探讨了以2-戊基-2-环戊烯酮为原料,以乙酰丙酮镍和三乙胺为催化剂以及在Me3SiCl作用下,烯丙基溴化锌与2-戊基-2-环戊烯酮的Michael加成反应,合成了2-戊基-3-烯丙基环戊酮,产率达74%。然后2-戊基-3-烯丙基环戊酮经过三氯化钌/高碘酸钠氧化、亚硫酰氯/甲醇酯化,得标题化合物。在适宜的条件下,3步反应总收率59%。

The Michael addition of allyzinc bromide to 2-pentyl-2-cyclopentenone was studied in the presence of Me3SiCl using Ni(acac)2 and tertiary amines as catalysts to give 2-pentyl-3-ally-cyclopentanone in 74% yield.Then 2-pentyl-3-ally-cyclopentanone was oxidized by NaIO4 using RuCl3 as the catalyst to give the target carboxylic acid,esterification of which gave methyl dihydrojasmonate.The overall product yield was 59% under proper reaction conditions.