Lewis acid catalyzed formation of tetrahydroquinolines via an intramolecular redox process.
Polycyclic tetrahydroquinolines were prepared by an efficient Lewis acid catalyzed 1,5-hydride shift, ring closure sequence. Gadolinium triflate was identified as a catalyst that is superior to scandium triflate as well as other Lewis acids. An approach toward a catalytic enantioselective variant is also described.
Murarka
Sandip
S
Department of Chemistry and Chemical Biology, Rutgers, The State University of New Jersey, Piscataway, New Jersey 08854, USA.
Zhang
Chen
C
Konieczynska
Marlena D
MD
Seidel
Daniel
D
D002384:Catalysis; D005682:Gadolinium / Q000737:chemistry*; D008698:Mesylates / Q000737:chemistry*; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D010084:Oxidation-Reduction; D011804:Quinolines / Q000138:chemical synthesis*; D013237:Stereoisomerism
D008698:Mesylates; D009942:Organometallic Compounds; D011804:Quinolines; D005682:Gadolinium; C012077:trifluoromethanesulfonic acid