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Paper | Special issue | Vol 95, No. 2, 2017, pp.1041-1073
Published online, 14th February, 2017
DOI: 10.3987/COM-16-S(S)76
Diastereoselective Synthesis of 2,4-Substituted Tetrahydroquinolines via Hf(OTf)4-Catalyzed Substitution/Cyclization of 2-Aminobenzyl Alcohols with Styrenes

Masahiro Noji,* Hiroto Kadowaki, Yuuki Kubota, Tomomi Yoshida, Noriko Saito, Subaru Yamaguchi, Ren Ohata, Keitaro Ishii, and Toshikatsu Takanami

*Department of Life and Pharmaceutical Sciences, Meiji Pharmaceutical University, 2-522-1 Noshio, Kiyose, Tokyo 204-8588, Japan


An efficient and convenient stereoselective synthetic approach to 2,4-substituted 1,2,3,4-tetrahydroquinoline has been developed. This catalytic procedure involves a sequential reaction of 2-aminobenzyl alcohol with styrenes in the presence of Hf(OTf)4 catalyst followed by intramolecular cyclization of the resulting cation species to give a variety of cis-2,4-substituted tetrahydroquinolines in good yield and diastereoselectivity.