A catalytic formal Si reaction was designed to achieve stereoretentive products for -4-hydroxymethyl-1,2-cyclopentene oxides by using diarylborinic acid as a dual role catalyst and chloride as a catalytic transient nucleophile through a double-displacement mechanism. This reaction offers the advantages of a low catalyst loading of 0.1 mol % and wide substrate scope, even including -substituents. The use of chiral boron acid as a catalyst for this reaction was also attempted.
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