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Diastereoselective synthesis of N-aryl tetrahydroquinolines and N-aryl indolines by the tandem reaction of arynes.

Research paper by Ji-Xin JX Pian, Lin L He, Guang-Fen GF Du, Hao H Guo, Bin B Dai

Indexed on: 23 May '14Published on: 23 May '14Published in: Journal of Organic Chemistry



Abstract

A 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.