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Multiple Hydrogen‐Bond Activation in Asymmetric Brønsted Acid Catalysis
Author(s) -
Liao HsuanHung,
Hsiao ChienChi,
Atodiresei Iuliana,
Rueping Magnus
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201800677
Subject(s) - stereocenter , brønsted–lowry acid–base theory , catalysis , chemistry , cycloaddition , hydrogen bond , combinatorial chemistry , enantioselective synthesis , stereochemistry , organic chemistry , molecule
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.