Asymmetric Synthesis of Cyclic Boronic Esters using Lithiation-Borylation

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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.