Nucleophilic Ring-Opening of Chlorooxiranes: A New Synthesis of α-Hydroxy α′-Substituted Ketones from Carbonyl Compounds and 1-Chloroalkyl<i>p</i>-Tolyl Sulfoxides
作者:Tsuyoshi Satoh、Asako Ogura、Youko Ikeda、Koji Yamakawa
DOI:10.1246/bcsj.64.1582
日期:1991.5
The addition of 1-chloroalkyl p-tolyl sulfoxides to carbonyl compounds gave adducts which were then converted to chlorooxiranes in two steps with good overall yields. The treatment of the chlorooxiranes with various nucleophiles gave α-hygroxy α′-substituted ketones or α-hydroxy ketones in good yields.
1-chloroalkyl p-tolyl sulfoxides 与羰基化合物的加成反应产生了加合物,然后通过两个步骤将其转化为氯环氧乙烷,总产率很高。用各种亲核剂处理氯环氧乙烷,可以得到α-羟基α′-取代酮或α-羟基酮,收率很高。