含酯基烯烃选择性硼氢化碘化反应——两种昆虫性信息素的合成

Selective Hydroboration-Iodination of Terminal Alkenes Containing Ester Groups——Synthesis of Two Insect Sex Pheromones

不饱和烃经硼氢化反应生成的硼烷在碱性及温和条件下与碘作用,可以获得产率较高的碘化物。然而,硼氢化碘化反应因需要强碱性条件而可能对许多对碱敏感基团产生不利影响,而且反应中需要过量硼烷。硼烷R3B中一般只有1～2个R基可以利用,反应产率以烯烃计算只有50％～65％,我们进行含酯末端烯烃的硼氢化碘化时。

Terminal alkenes containing ester groups are converted to w-functional alkyl iodides through a hydroboration-iodihation reaction blinder a mild condition; All Of the three alkyl groups on borane can be used in this case. The insect sex pheromones of Tortrix Viridana and Adoxophes Orana Rod are synthesized in a higher (Z)-form purity by using the w-functiori terminal alkyl iodides.