Asymmetric Synthesis of Cyclic Boronic Esters using Lithiation-Borylation

环丁烷具有结构刚性，其取代基具有明确的空间排列，具有多种生物活性。该项目的目的是开发一种高效的具有高度通用的硼酸酯取代基的环丁烷的不对称合成方法。合成将通过高烯丙基醇衍生的硼酸酯的锂化合成的五元环硼酸络合物的环收缩来进行。对映体高烯丙醇的易获得性以及同源异构化用于增加环的尺寸和在环形成之前安装额外的手性的可能性使该方法特别吸引人。

Cyclobutanes have a structural rigidity which provides a well-defined spatial arrangement of their substituents and gives rise to diverse bioactivities.The aim of the project is to develop an efficient asymmetric synthesis of cyclobutanes with a highly versatile boronic ester substituent. The synthesis will proceed via the ring contraction of a 5-membered ring boronate complex formed by lithiation-borylation of a homoallylic alcohol derived boronic ester. The easy accessibility of enantiopure homoallylic alcohols and the potential of homologation to be used for increasing ring size and installing additional chirality before ring formation makes this method particularly attractive.The use of this method for the medicinally relevant materials will also be investigated in collaboration with Bayer.