期刊论文

Liu, Siyuan

Zhang, WZ; Wang, BM (reprint author), Dalian Univ Technol, Sch Chem, Sch Pharmaceut Sci & Technol, State Key Lab Fine Chem, Dalian 116024, Peoples R China.

Zhang, Wenzhu,Qu, Jingping,Wang, Baomin

2018-10-21

ORGANIC CHEMISTRY FRONTIERS

SCIE

J

5

20

3008-3012

2052-4129

New reactivity and application of 2-methyl indolenines have been established by their engagement in a tandem condensation/1,5-hydride transfer/cyclization process. Under the catalysis of BF3Et2O, the condensation of easily available 2-methyl indolenines with o-amino benzaldehydes occurred readily, followed by a facile redox neutral 1,5-hydride shift/cyclization process in a one-pot manner, leading to the construction of a novel indolenine-tetrahydroquinoline assembly in good yield with high levels of diastereoselectivity. This synthetic protocol tolerates a broad range of substrates in terms of both the indolenine and o-amino benzaldehyde partners. The reaction can be readily scaled up and the indolenine moiety of the product can be facilely reduced to the indoline scaffold.