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Updated: Feb 11, 2026

Preparation of Silica Nanoparticles Through Microwave-assisted Acid-catalysis
Published on: December 16, 2013
Multiple Hydrogen-Bond Activation in Asymmetric Brønsted Acid Catalysis
Hsuan-Hung Liao1, Chien-Chi Hsiao1, Iuliana Atodiresei1
1Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074, Aachen, Germany.
Abstract:
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.
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