Nucleophilic Substitution of the Hydroxyl Group in Stereogenic Alcohols with Chirality Transfer

作者：Bunrit, Anon; Dahlstrand, Christian; Srifa, Pemikar; Olsson, Sandra K.; Huang, Genping; Biswas, Srijit; Himo, Fahmi; Samec, Joseph S. M.^*

来源：Synlett, 2016, 27(2): 173-176.

DOI：10.1055/s-0035-1560494

• green chemistry
• BrOnsted acid
• base catalysis
• chirality transfer
• nucleophilic substitutions
• asymmetric synthesis
• mechanistic studies
• DFT calculations

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 S(N)2-type reaction mechanism.

• 出版日期2016-1
• 单位天津大学