Palladium(0)-Catalyzed Allylation of 2,2′-Dihydroxybiphenyl by 1-Ethenylcyclopropyl Sulfonates: Preparation of 2,2′-Bis(cyclopropylideneethoxy) biphenyls
作者:Giovanna Delogu、Jacques Salaün、Cristina de Candia、Davide Fabbri、Pier Paolo Piras、Jean Ollivier
DOI:10.1055/s-2002-34950
日期:——
Dipotassium salts of 2,2 -dihydroxybiphenyl derivatives underwent palladium(0) catalyzed regioselective allylation by sul- fonic esters (mesylates, tosylates) of 1-ethenylcyclopropanol to pro- duce, in good yields, 2,2 -bis(cyclopropylideneethoxy)biphenyls, which are of biological interest. Whilst the tetrapotassium salt of 2,2 ,6,6 -tetrahydroxybiphenyl, formed the triadduct 2,2 -tris(cyclo- prop
2,2-二羟基联苯衍生物的二钾盐通过 1-乙烯基环丙醇的磺酸酯(甲磺酸盐、甲苯磺酸盐)进行钯 (0) 催化的区域选择性烯丙基化反应,以良好的收率生成 2,2-双(亚环丙基乙氧基)联苯,具有生物学意义。而2,2,6,6-四羟基联苯的四钾盐则形成其主要产物2,2-三(环亚丙基乙氧基)羟基联苯三加合物。发生了意外的钯诱导的单加合物 2-(2- 亚环丙基乙氧基)-2-羟基联苯衍生物重排为 2-(2-(1-乙烯基环丙氧基))-2-羟基联苯衍生物;而单加合物 2- ((2-cyclopropidene-1-trimethylsilyl)ethoxy)-6,6-dimethoxy-2- hydroxybiphenyl 的次要非对映异构体在 CDCl3 中放置后,经过 Claisen 重排成 2,