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Indexed by:期刊论文

Date of Publication:2018-10-21

Journal:ORGANIC CHEMISTRY FRONTIERS

Included Journals:SCIE

Volume:5

Issue:20

Page Number:3008-3012

ISSN No.:2052-4129

Abstract: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.