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dc.contributor.authorLiao, Hsuan-Hung
dc.contributor.authorHsiao, Chien-Chi
dc.contributor.authorAtodiresei, Iuliana
dc.contributor.authorRueping, Magnus
dc.date.accessioned2018-05-08T07:17:55Z
dc.date.available2018-05-08T07:17:55Z
dc.date.issued2018-05-03
dc.identifier.citationLiao H-H, Hsiao C-C, Atodiresei I, Rueping M (2018) Multiple Hydrogen-Bond Activation in Asymmetric Brønsted Acid Catalysis. Chemistry - A European Journal. Available: http://dx.doi.org/10.1002/chem.201800677.
dc.identifier.issn0947-6539
dc.identifier.doi10.1002/chem.201800677
dc.identifier.urihttp://hdl.handle.net/10754/627775
dc.description.abstractAn efficient protocol for the asymmetric synthesis of chiral tetrahydroquinolines bearing multiple stereogenic centers by means of asymmetric Brønsted acid catalysis was developed. A chiral 1,1′-spirobiindane-7,7′-diol (SPINOL)-based N-triflylphosphoramide (NTPA) proved to be an effective Brønsted acid catalyst for the in situ generation of aza-ortho-quinone methides (aza-o-QMs) and their subsequent cycloaddition reaction with unactivated alkenes to provide the products with excellent diastereo- and enantioselectivities. In addition, DFT calculations provided insight into the activation mode and nature of the interactions between the N-triflylphosphoramide catalyst and the generated aza-o-QMs.
dc.description.sponsorshipFinancial support by the DFG is gratefully acknowledged.
dc.publisherWiley
dc.relation.urlhttps://onlinelibrary.wiley.com/doi/full/10.1002/chem.201800677
dc.rightsArchived with thanks to Chemistry - A European Journal
dc.subjectBrønsted acids
dc.subjectcycloaddition
dc.subjectnitrogen heterocycles
dc.subjectorganocatalysis
dc.subjectreactive intermediates
dc.titleMultiple Hydrogen-Bond Activation in Asymmetric Brønsted Acid Catalysis
dc.typeArticle
dc.contributor.departmentChemical Science Program
dc.contributor.departmentKAUST Catalysis Center (KCC)
dc.contributor.departmentPhysical Science and Engineering (PSE) Division
dc.identifier.journalChemistry - A European Journal
dc.eprint.versionPost-print
dc.contributor.institutionInstitute of Organic Chemistry; RWTH Aachen University; Landoltweg 1 52074 Aachen Germany
kaust.personRueping, Magnus
refterms.dateFOA2019-05-03T00:00:00Z
dc.date.published-online2018-05-03
dc.date.published-print2018-05-28


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