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Enantioselective Assembly of Congested Cyclopropanes using Redox-Active Aryldiazoacetates
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.ORCID iD: 0000-0001-9199-6736
Number of Authors: 22019 (English)In: ACS Catalysis, ISSN 2155-5435, E-ISSN 2155-5435, Vol. 9, no 9, p. 7870-7875Article in journal (Refereed) Published
Abstract [en]

The enantioselective assembly of quaternary stereocenters through sequential functionalization of versatile carbon-atom precursors has the potential to systematize the synthesis of these ubiquitous stereogenic elements. Herein, we report two catalytic processes that allow the realization of this concept in the enantioselective synthesis of cyclopropanes. We demonstrate that C-H functionalization, carbene-transfer, and decarboxylative cross-coupling can sequentially take place in the same carbon atom to obtain highly enantioenriched cyclopropane products. The reactions reported herein give access to redox-active analogues of privileged aryldiazoacetates and demonstrate their enantioselective carbene transfer with a simple and practical rhodium catalyst.

Place, publisher, year, edition, pages
2019. Vol. 9, no 9, p. 7870-7875
Keywords [en]
asymmetric catalysis, C-H arylation, cyclopropanes, quaternary centers, carbenes
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:su:diva-174961DOI: 10.1021/acscatal.9b02615ISI: 000485090400024OAI: oai:DiVA.org:su-174961DiVA, id: diva2:1365033
Available from: 2019-10-23 Created: 2019-10-23 Last updated: 2019-10-23Bibliographically approved

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