1,2-Metallate Rearrangement as a Toolbox for the Synthesis of Allylic Alcohols,The Journal of Organic Chemistry

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1,2-Metallate Rearrangement as a Toolbox for the Synthesis of Allylic Alcohols
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2023-08-18 , DOI: 10.1021/acs.joc.3c01309
Yannick Linne ₁ , Daniel Lohrberg ₁ , Henry Struwe ₁ , Elvira Linne ₁ , Anastasia Stohwasser ₁ , Markus Kalesse _{1,

2}

Affiliation

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.

中文翻译：

1,2-金属盐重排作为烯丙醇合成的工具箱

合成生物活性物质的新方法和方案的开发仍然是有机化学最重要的支柱之一，而这些特殊的结构基序之一就是烯丙醇。迄今为止，选择的合成方法是野崎-桧山-高井-岸反应。我们在这里描述了一种通过 1,2-金属化物重排合成烯丙醇的有价值的替代方案。在这项工作中，具有不同官能团的各种乙烯基硼酸酯已应用于 Hoppe-Matteson-Aggarwal 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。

更新日期：2023-08-18

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