Multiple Hydrogen-Bond Activation in Asymmetric Brønsted Acid Catalysis
KAUST DepartmentChemical Science Program
KAUST Catalysis Center (KCC)
Physical Science and Engineering (PSE) Division
Online Publication Date2018-05-03
Print Publication Date2018-05-28
Permanent link to this recordhttp://hdl.handle.net/10754/627775
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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.
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.
SponsorsFinancial support by the DFG is gratefully acknowledged.
JournalChemistry - A European Journal