Multiple Hydrogen-Bond Activation in Asymmetric Brønsted Acid Catalysis

Hsuan-Hung Liao, Chien-Chi Hsiao, Iuliana Atodiresei, Magnus Rueping

Research output: Contribution to journalArticlepeer-review

13 Scopus citations

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.
Original languageEnglish (US)
Pages (from-to)7718-7723
Number of pages6
JournalChemistry - A European Journal
Volume24
Issue number30
DOIs
StatePublished - May 3 2018

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