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Convenient Access to Chiral Cyclobutanes with Three Contiguous Stereocenters from Verbenone by Directed C(sp(3))-H arylation
Stockholm University, Faculty of Science, Department of Organic Chemistry. RWTH Aachen, Germany.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.ORCID iD: 0000-0001-9329-0091
Stockholm University, Faculty of Science, Department of Organic Chemistry.ORCID iD: 0000-0002-3153-748X
Number of Authors: 42019 (English)In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 25, no 20, p. 5154-5157Article in journal (Refereed) Published
Abstract [en]

This work demonstrates how a series of complex, chiral cyclobutane derivatives can be accessed in four steps from the terpene verbenone through the application of a directed C-H functionalization approach. The developed synthetic route involved an 8-aminoquinoline-directed C(sp(3))-H arylation as the key step, and this reaction could be carried out with a wide range of aryl and heteroaryl iodides to furnish a variety of cyclobutane products with three contiguous stereocenters. Moreover, it was shown that the 8-aminoquinoline auxiliary could be effectively removed from the cyclobutane derivatives using an ozonolysis-based cleavage method.

Place, publisher, year, edition, pages
2019. Vol. 25, no 20, p. 5154-5157
Keywords [en]
8-aminoquinoline, C(sp(3))-H functionalization, cyclobutanes, palladium, verbenone
National Category
Chemical Sciences
Identifiers
URN: urn:nbn:se:su:diva-170158DOI: 10.1002/chem.201806416ISI: 000468855200007PubMedID: 30716181OAI: oai:DiVA.org:su-170158DiVA, id: diva2:1330369
Available from: 2019-06-25 Created: 2019-06-25 Last updated: 2019-12-03Bibliographically approved

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