通过硼氢化/原硼烷化方法高立体选择性合成顺式链烯基频哪醇硼酸酯和顺式链烯基三氟硼酸钾。
Highly stereoselective synthesis of cis-alkenyl pinacolboronates and potassium cis-alkenyltrifluoroborates via a hydroboration/protodeboronation approach.
作者信息
Molander Gary A, Ellis Noel M
机构信息
Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104-6323, USA.
出版信息
J Org Chem. 2008 Sep 5;73(17):6841-4. doi: 10.1021/jo801191v. Epub 2008 Aug 6.
Abstract
A number of alkynyl pinacolboronates bearing various functional groups were synthesized according to literature methods. These were then stereoselectively reduced to the cis-alkenyl pinacolboronates via hydroboration with dicyclohexylborane followed by chemoselective protodeboronation using acetic acid. Treatment with potassium hydrogen fluoride smoothly converted these to the corresponding potassium organotrifluoroborates.
摘要
根据文献方法合成了一系列带有各种官能团的炔基频哪醇硼酸酯。然后通过用二环己基硼烷进行硼氢化反应，接着使用乙酸进行化学选择性原硼氢化反应，将这些化合物立体选择性地还原为顺式烯基频哪醇硼酸酯。用氟化钾处理可顺利地将它们转化为相应的有机三氟硼酸钾。
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