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dc.contributor.authorEl-Sepelgy, Osama
dc.contributor.authorBrzozowska, Aleksandra
dc.contributor.authorAzofra Mesa, Luis
dc.contributor.authorJang, Yoon Kyung
dc.contributor.authorCavallo, Luigi
dc.contributor.authorRueping, Magnus
dc.date.accessioned2018-01-01T12:19:03Z
dc.date.available2018-01-01T12:19:03Z
dc.date.issued2017-10-24
dc.identifier.citationEl-Sepelgy O, Brzozowska A, Azofra LM, Jang YK, Cavallo L, et al. (2017) Experimental and Computational Study of an Unexpected Iron-Catalyzed Carboetherification by Cooperative Metal and Ligand Substrate Interaction and Proton Shuttling. Angewandte Chemie International Edition 56: 14863–14867. Available: http://dx.doi.org/10.1002/anie.201708240.
dc.identifier.issn1433-7851
dc.identifier.doi10.1002/anie.201708240
dc.identifier.doi10.1002/ange.201708240
dc.identifier.urihttp://hdl.handle.net/10754/626621
dc.description.abstractAn iron-catalyzed cycloisomerization of allenols to deoxygenated pyranose glycals has been developed. Combined experimental and computational studies show that the iron complex exhibits a dual catalytic role in that the non-innocent cyclopentadienone ligand acts as proton shuttle by initial hydrogen abstraction from the alcohol and by facilitating protonation and deprotonation events in the isomerization and demetalation steps. Molecular orbital analysis provides insight into the unexpected and selective formation of the 3,4-dihydro-2H-pyran.
dc.description.sponsorshipL.M.A. and L.C. acknowledge King Abdullah University of Science and Technology (KAUST) for support. Gratitude is also due to the KAUST Supercomputing Laboratory for providing the computational resources (use of the supercomputer Shaheen II).
dc.publisherWiley-Blackwell
dc.relation.urlhttp://onlinelibrary.wiley.com/doi/10.1002/anie.201708240/full
dc.rightsThis is the peer reviewed version of the following article: Experimental and Computational Study of an Unexpected Iron-Catalyzed Carboetherification by Cooperative Metal and Ligand Substrate Interaction and Proton Shuttling, which has been published in final form at http://doi.org/10.1002/anie.201708240. This article may be used for non-commercial purposes in accordance With Wiley Terms and Conditions for self-archiving.
dc.subjectcarboetherification
dc.subjectenol ethers
dc.subjectheterocycles
dc.subjectiron catalysis
dc.subjectsynthetic methods
dc.titleExperimental and Computational Study of an Unexpected Iron-Catalyzed Carboetherification by Cooperative Metal and Ligand Substrate Interaction and Proton Shuttling
dc.typeArticle
dc.contributor.departmentChemical Science Program
dc.contributor.departmentKAUST Catalysis Center (KCC)
dc.contributor.departmentPhysical Science and Engineering (PSE) Division
dc.identifier.journalAngewandte Chemie International Edition
dc.eprint.versionPost-print
dc.contributor.institutionInstitute of Organic Chemistry; RWTH Aachen University; Landoltweg 1 52074 Aachen Germany
kaust.personAzofra Mesa, Luis
kaust.personCavallo, Luigi
kaust.personRueping, Magnus
kaust.acknowledged.supportUnitSupercomputing Laboratory
dc.date.published-online2017-10-24
dc.date.published-print2017-11-20


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