Linne Yannick, Lohrberg Daniel, Struwe Henry, Linne Elvira, Stohwasser Anastasia, Kalesse Markus
Institute of Organic Chemistry, Gottfried Wilhelm Leibniz Universität Hannover, 30167 Hannover, Germany.
Centre of Biomolecular Drug Research (BMWZ), Gottfried Wilhelm Leibniz Universität Hannover, 30167 Hannover, Germany.
J Org Chem. 2023 Sep 1;88(17):12623-12629. doi: 10.1021/acs.joc.3c01309. Epub 2023 Aug 18.
The development of new methods and protocols for the synthesis of biologically active substances remains one of the most important pillars in organic chemistry, and one of these privileged structural motifs are allylic alcohols. The method of choice to date for the synthesis of these is the Nozaki-Hiyama-Takai-Kishi reaction. We describe here a valuable alternative to the synthesis of allylic alcohols via 1,2-metallate rearrangement. In this work, various vinyl boronic esters with different functional groups have been applied in the Hoppe-Matteson-Aggarwal reaction. In addition, two monoterpenoids were constructed via this convergent synthetic strategy.
开发用于合成生物活性物质的新方法和新方案仍然是有机化学中最重要的支柱之一，而烯丙醇就是其中一种具有特殊结构的基序。迄今为止，合成这些烯丙醇的首选方法是野崎-桧山-高木-岸反应。我们在此描述了一种通过1,2-金属酸酯重排合成烯丙醇的有价值的替代方法。在这项工作中，各种带有不同官能团的乙烯基硼酸酯已应用于霍普-马特森-阿加瓦尔反应。此外，通过这种收敛合成策略构建了两种单萜类化合物。
