Please use this identifier to cite or link to this item: http://doi.org/10.25358/openscience-10141
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dc.contributor.authorSietmann, Jan-
dc.contributor.authorTenberge, Marius-
dc.contributor.authorWahl, Johannes M.-
dc.date.accessioned2024-03-01T11:28:52Z-
dc.date.available2024-03-01T11:28:52Z-
dc.date.issued2022-
dc.identifier.urihttps://openscience.ub.uni-mainz.de/handle/20.500.12030/10159-
dc.description.abstractMethylenecyclobutanes are found to undergo Wacker oxidation via a semi-pinacol-type rearrangement. Key to a successful process is the use of tert-butyl nitrite as oxidant, which not only enables efficient catalyst turn-over but also ensures high Markovnikov-selectivity under mild conditions. Thus, cyclopentanones (26 examples) can be accessed in an overall good yield and excellent selectivity (up to 97 % yield, generally >99 : 1 ketone:aldehyde ratio). Stereochemical analysis of the reaction sequence reveals migration aptitudes in line with related 1,2-shifts. By introducing a pyox ligand to palladium, prochiral methylenecyclobutanes can be desymmetrized, thus realizing the first enantioselective Wacker oxidation.en_GB
dc.language.isoengde
dc.rightsCC BY*
dc.rights.urihttps://creativecommons.org/licenses/by/4.0/*
dc.subject.ddc540 Chemiede_DE
dc.subject.ddc540 Chemistry and allied sciencesen_GB
dc.titleWacker oxidation of methylenecyclobutanes : scope and selectivity in an unusual settingen_GB
dc.typeZeitschriftenaufsatzde
dc.identifier.doihttp://doi.org/10.25358/openscience-10141-
jgu.type.contenttypeScientific articlede
jgu.type.dinitypearticleen_GB
jgu.type.versionPublished versionde
jgu.type.resourceTextde
jgu.organisation.departmentFB 09 Chemie, Pharmazie u. Geowissensch.de
jgu.organisation.number7950-
jgu.organisation.nameJohannes Gutenberg-Universität Mainz-
jgu.rights.accessrightsopenAccess-
jgu.journal.titleAngewandte Chemie International Editionde
jgu.journal.volume62de
jgu.journal.issue7de
jgu.pages.alternativee202215381de
jgu.publisher.year2022-
jgu.publisher.nameWileyde
jgu.publisher.placeWeinheimde
jgu.publisher.issn1521-3773de
jgu.organisation.placeMainz-
jgu.subject.ddccode540de
jgu.publisher.doi10.1002/anie.202215381de
jgu.organisation.rorhttps://ror.org/023b0x485-
jgu.subject.dfgNaturwissenschaftende
jgu.relation.IsVersionOf10.25358/openscience-10142-
Appears in collections:DFG-491381577-H

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