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Diastereoselective Synthesis of N‑Aryl Tetrahydroquinolines and N‑Aryl Indolines by the Tandem Reaction of Arynes
journal contribution
posted on 2014-06-20, 00:00 authored by Ji-Xin Pian, Lin He, Guang-Fen Du, Hao Guo, Bin DaiA tandem reaction of arynes with
α- or β-amino ketones
has been revealed. Arynes react with β-amino ketones through
a cascade insertion–cyclization process to afford N-aryl tetrahydroquinolines in good yield with excellent anti-selectivity. Meanwhile, the coupling of arynes with α-amino
ketones produces multisubstituted indolines in high yield with syn-selectivity. A quaternary carbon center can be constructed
in this process, and the reaction can be easily scaled up.