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Preparation of Chiral Enantioenriched Densely Substituted Cyclopropyl Azoles, Amines, and Ethers via Formal SN2′ Substitution of Bromocylopropanes

dc.contributor.authorStraub, Hillary
dc.contributor.authorRyabchuk, Pavel
dc.contributor.authorRubina, Marina
dc.contributor.authorRubin, Michael
dc.date.accessioned2023-02-14T19:45:58Z
dc.date.available2023-02-14T19:45:58Z
dc.date.issued2022-10-20
dc.identifier.citationStraub, H.; Ryabchuk, P.; Rubina, M.; Rubin, M. Preparation of Chiral Enantioenriched Densely Substituted Cyclopropyl Azoles, Amines, and Ethers via Formal SN2′ Substitution of Bromocylopropanes. Molecules 2022, 27, 7069. https://doi.org/10.3390/molecules27207069en_US
dc.identifier.urihttp://hdl.handle.net/1808/33799
dc.description.abstractEnantiomerically enriched cyclopropyl ethers, amines, and cyclopropylazole derivatives possessing three stereogenic carbon atoms in a small cycle are obtained via the diastereoselective, formal nucleophilic substitution of chiral, non-racemic bromocyclopropanes. The key feature of this methodology is the utilization of the chiral center of the cyclopropene intermediate, which governs the configuration of the two adjacent stereocenters that are successively installed via 1,4-addition/epimerization sequence.en_US
dc.publisherMDPIen_US
dc.rights© 2022 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license.en_US
dc.rights.urihttp://creativecommons.org/licenses/by/4.0/en_US
dc.subjectCyclopropenesen_US
dc.subjectCyclopropanesen_US
dc.subjectNucleophilic additionen_US
dc.subjectMetal-templated reactionsen_US
dc.titlePreparation of Chiral Enantioenriched Densely Substituted Cyclopropyl Azoles, Amines, and Ethers via Formal SN2′ Substitution of Bromocylopropanesen_US
dc.typeArticleen_US
kusw.kuauthorStraub, Hillary
kusw.kuauthorRyabchuk, Pavel
kusw.kuauthorRubina, Marina
kusw.kuauthorRubin, Michael
kusw.kudepartmentChemistryen_US
dc.identifier.doi10.3390/molecules27207069en_US
dc.identifier.orcidhttps://orcid.org/0000-0003-2859-3867en_US
dc.identifier.orcidhttps://orcid.org/0000-0002-1668-9311en_US
kusw.oaversionScholarly/refereed, publisher versionen_US
kusw.oapolicyThis item meets KU Open Access policy criteria.en_US
dc.identifier.pmidPMC9609026en_US
dc.rights.accessrightsopenAccessen_US


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© 2022 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license.
Except where otherwise noted, this item's license is described as: © 2022 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license.