通过[1,5]-烷基硫基基团转移介导的骨架重排构建 1,3-二硫代四氢萘。
Construction of 1,3-Dithio-Substituted Tetralins by [1,5]-Alkylthio Group Transfer Mediated Skeletal Rearrangement.
机构信息
Department of Applied Chemistry, Graduate School of Engineering , Tokyo University of Agriculture and Technology , 2-24-16 Nakacho , Koganei , Tokyo 184-8588 , Japan.
Department of Chemistry and Research Center for Smart Molecules , Rikkyo University , 3-34-1 Nishi-Ikebukuro , Toshima-ku, Tokyo 171-8501 , Japan.
出版信息
Org Lett. 2018 Jul 20;20(14):4223-4226. doi: 10.1021/acs.orglett.8b01610. Epub 2018 Jun 29.
A novel skeletal rearrangement involving a [1,5]-alkylthio group transfer/cyclization sequence is described. Treatment of benzylidene malonates having a thioketal moiety at the homobenzyl position with a catalytic amount of Sc(OTf) afforded alkylthio group rearranged adducts in good chemical yields. Detailed investigation of the reaction mechanism revealed that an intramolecular conjugate addition/ring opening sequence (not through-space transfer) is the key to achieving this reaction.
描述了一种涉及[1,5]-烷基硫醚基团转移/环化序列的新型骨架重排反应。用催化量的 Sc(OTf) 处理具有偕二苄基位置上的硫缩酮部分的苄叉丙二酸酯，以良好的化学收率得到了烷基硫醚重排加合物。对反应机理的详细研究表明，分子内共轭加成/开环序列（不是通过空间转移）是实现该反应的关键。
Zotero 插件