TY - JOUR
T1 - Multiple Hydrogen-Bond Activation in Asymmetric Brønsted Acid Catalysis
AU - Liao, Hsuan-Hung
AU - Hsiao, Chien-Chi
AU - Atodiresei, Iuliana
AU - Rueping, Magnus
N1 - KAUST Repository Item: Exported on 2020-10-01
Acknowledgements: Financial support by the DFG is gratefully acknowledged.
PY - 2018/5/3
Y1 - 2018/5/3
N2 - An 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.
AB - An 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.
UR - http://hdl.handle.net/10754/627775
UR - https://onlinelibrary.wiley.com/doi/full/10.1002/chem.201800677
UR - http://www.scopus.com/inward/record.url?scp=85046349030&partnerID=8YFLogxK
U2 - 10.1002/chem.201800677
DO - 10.1002/chem.201800677
M3 - Article
SN - 0947-6539
VL - 24
SP - 7718
EP - 7723
JO - Chemistry - A European Journal
JF - Chemistry - A European Journal
IS - 30
ER -