用膦基取代的钯π-烯丙基配合物捕获半缩醛用于合成取代环醚。
Trapping Hemiacetals with Phosphono Substituted Palladium π-Allyl Complexes for the Synthesis of Substituted Cyclic Ethers.
作者信息
Sutivisedsak Nongnuch, Dawadi Surendra, Spilling Christopher D
机构信息
Department of Chemistry and Biochemistry, University of Missouri - St. Louis, One University Boulevard, St. Louis, Missouri, 63121, USA.
出版信息
Tetrahedron Lett. 2015 Jun 3;56(23):3534-3537. doi: 10.1016/j.tetlet.2015.01.050.
Abstract
Oxidation of hydroxy substituted phosphono allylic carbonates gave the aldehyde substituted phosphonates in good yield. Stereospecific palladium (0)-catalyzed cyclization in the presence of methanol or water gave acetal tetrahydrofuran and tetrahydropyran vinyl phosphonate products derived from hemiacetal trapping. The tetrahydrofuran acetals undergo Lewis acid catalyzed addition of nucleophiles to give diastereoisomeric mixtures of substituted tetrahydrofurans.
摘要
羟基取代的膦酰基烯丙基碳酸酯的氧化反应以良好的产率得到醛取代的膦酸酯。在甲醇或水存在下，立体专一性的钯（0）催化环化反应得到源自半缩醛捕获的缩醛四氢呋喃和四氢吡喃乙烯基膦酸酯产物。四氢呋喃缩醛在路易斯酸催化下进行亲核试剂加成反应，生成取代四氢呋喃的非对映异构体混合物。
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