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Synlett 2016; 27(02): 173-176
DOI: 10.1055/s-0035-1560494
DOI: 10.1055/s-0035-1560494
synpacts
Nucleophilic Substitution of the Hydroxyl Group in Stereogenic Alcohols with Chirality Transfer
Further Information
Publication History
Received: 26 August 2015
Accepted after revision: 16 September 2015
Publication Date:
15 October 2015 (online)
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 Brønsted 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 Brønsted acid operates in a bifunctional manner to promote an SN2-type reaction mechanism.
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