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Nucleophilic Substitution of the Hydroxyl Group in Stereogenic Alcohols with Chirality Transfer
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC.
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC.
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC.
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC.
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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
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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
Organic Chemistry
Identifiers
URN: urn:nbn:se:uu:diva-276873DOI: 10.1055/s-0035-1560494ISI: 000368131300004OAI: oai:DiVA.org:uu-276873DiVA: diva2:903710
Funder
Swedish Research CouncilStiftelsen Olle Engkvist ByggmästareWenner-Gren FoundationsGöran Gustafsson Foundation for promotion of scientific research at Uppala University and Royal Institute of TechnologyKnut and Alice Wallenberg Foundation
Available from: 2016-02-16 Created: 2016-02-16 Last updated: 2017-11-30Bibliographically approved

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Olsson, Sandra K.

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