Abstract
A brief overview of the development of direct substitution of the hydroxyl (OH) group of alcohols in our research group is presented. By applying a Bronsted acid, an intramolecular substitution of the OH group in stereogenic alcohols with chirality transfer was achieved. Noteworthy, the intramolecular substitution has a wide scope in respect to both the nucleophile and also the nucleofuge. A mechanistic study by both experiments and DFT calculations revealed a unique reaction pathway in which the Bronsted acid operates in a bifunctional manner to promote an SN2-type reaction mechanism.
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