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Nucleophilic Substitution of the Hydroxyl Group in Stereogenic Alcohols with Chirality Transfer
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Number of Authors: 8
2016 (English)In: Synlett: Accounts and Rapid Communications in Synthetic Organic Chemistry, ISSN 0936-5214, E-ISSN 1437-2096, Vol. 27, no 2, 173-176 p.Article in journal (Refereed) Published
Abstract [en]

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.

Place, publisher, year, edition, pages
2016. Vol. 27, no 2, 173-176 p.
Keyword [en]
green chemistry, BrOnsted acid, base catalysis, chirality transfer, nucleophilic substitutions, asymmetric synthesis, mechanistic studies, DFT calculations
National Category
Chemical Sciences
Identifiers
URN: urn:nbn:se:su:diva-126782DOI: 10.1055/s-0035-1560494ISI: 000368131300004OAI: oai:DiVA.org:su-126782DiVA: diva2:943964
Available from: 2016-06-28 Created: 2016-02-15 Last updated: 2016-06-28Bibliographically approved

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Huang, GenpingHimo, FahmiSamec, Joseph S. M.
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Department of Organic Chemistry
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