Stereoselective One-pot Dialkylation of<i>gem</i>-Dihalocyclopropanes by Means of Dialkylcopperlithiums
作者:Katuzi Kitatani、Tamejiro Hiyama、Hitosi Nozaki
DOI:10.1246/bcsj.50.1600
日期:1977.6
(2 and 3) is established by successive treatment with dibutylcopperlithium and several electrophiles. This sequence is found to be stereochemically controllable and is successfully applied to dl-sirenin synthesis. In contrast to the reaction of dibutylcopperlithium, dimethyl- and divinylcopperlithiums convert 1,1-dibromo-2-phenylcyclopropane (1a) into 1-bromo-1-methyl- and 1-bromo-1-vinyl-2-phenylcyclopropanes
通过用二丁基锂锂和几种亲电子试剂连续处理,可将偕二卤代环丙烷 (1) 转化为 1-烷基-1-丁基环丙烷 (2 和 3)。发现该序列是立体化学可控的,并成功应用于 dl-sirenin 合成。与二丁基铜锂的反应相反,二甲基和二乙烯基铜锂将 1,1-二溴-2-苯基环丙烷 (1a) 转化为 1-溴-1-甲基-和 1-溴-1-乙烯基-2-苯基环丙烷(15a、16a和 15b、16b)。