论文成果
Engaging 2-methyl indolenines in a tandem condensation/1,5-hydride transfer/cyclization process: construction of a novel indolenine-tetrahydroquinoline assembly
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- 论文类型：期刊论文
- 发表时间：2018-10-21
- 发表刊物：ORGANIC CHEMISTRY FRONTIERS
- 收录刊物：SCIE
- 文献类型：J
- 卷号：5
- 期号：20
- 页面范围：3008-3012
- ISSN号：2052-4129
- 摘要：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.
