Multiple Hydrogen-Bond Activation in Asymmetric Brønsted Acid Catalysis
KAUST DepartmentPhysical Sciences and Engineering (PSE) Division
Chemical Science Program
KAUST Catalysis Center (KCC)
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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