Two-Step Method for Constructing a Quaternary Carbon Atom with a Geminal Divinyl Group from a Ketone
Two-Step Method for Constructing a Quaternary Carbon Atom with a Geminal Divinyl Group from a Ketone
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从酮构建具有偕二乙烯基的季碳原子的两步法
DOI：
10.1021/acs.orglett.2c01799
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发表时间：
2022
期刊：
影响因子：
5.2
通讯作者：
Tanino Keiji
中科院分区：
文献类型：
--
作者：
Ogura Ryota;Satoh Kazuto;Kiuchi Wataru;Kato Kosuke;Ikeuchi Kazutada;Suzuki Takahiro;Tanino Keiji
以酮为原料，采用两步法合成偕二乙烯基化合物。使由1-苯硫基-4-三甲基甲硅烷基-2-丁烯制备的烯丙基钛试剂与酮反应，并且使所得叔醇经历布朗斯台德酸介导的重排反应以生成偕二乙烯基化合物。引入另一个烯烃部分，然后进行闭环复分解，得到在桥头位置具有乙烯基的双环化合物。
A two-step synthesis of geminal divinyl compounds from ketones was developed. An allyl titanium reagent prepared from 1-phenylthio-4-trimethylsilyl-2-butene was reacted with a ketone, and the resulting tertiary alcohol was subjected to a Brønsted acid-mediated rearrangement reaction to generate a geminal divinyl compound. Introduction of another alkene moiety followed by ring closing metathesis resulted in a bicyclic compound possessing a vinyl group at the bridgehead position.