The invention provides a preparation method of a chiral benzyl borate compound, and belongs to the technical field of preparation of organic compounds, and the preparation method comprises the following steps: mixing a p-
methylene benzoquinone compound, bis (pinacolato) diboron, a Bolm
chiral ligand, a PS-CS-SiO2 (at) Cu catalytic material and a reaction
solvent, stirring, reacting for set time, carrying out reduced pressure suction
filtration after the reaction is completed, and
drying to obtain the chiral benzyl borate compound. Filtering to obtain filtrate and filter residues; sequentially extracting the filtrate by using
ethyl acetate and a saturated
saline solution, then
drying an organic phase by using
anhydrous Na2SO4, carrying out reduced-pressure suction
filtration, and carrying out rotary
drying to obtain a crude product; and carrying out
thin layer chromatography purification on the crude product to obtain the 1, 6-chiral benzyl borate compound. The raw materials used in the invention are cheap and easily available, the synthesis operation steps are simple, the
reaction conditions are mild, the obtained 1, 6-chiral benzyl borate compound has high yield and enantioselectivity, and the catalytic material can be biologically degraded and recycled.