期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 84, 期 12, 页码 7829-7839出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.9b00710
关键词
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资金
- National Natural Science Foundation of China [21772069, 21702077, 21831007]
- Natural Science Foundation of Jiangsu Province [BK20160003, BK20170227]
- Young Medical Talents Project of Jiangsu Province [QNRC2016571]
- Six Kinds of Talents Project of Jiangsu Province [SWYY-025]
- Undergraduate Project of Jiangsu Province [201810320049Z]
A catalytic asymmetric conjugate addition of indoles to o-hydroxyphenyl substituted p-quinone methides has been established in the presence of chiral phosphoric acid, which afforded chiral indole-containing triarylmethanes in generally high yields (54-98%) and good enantioselectivities (90:10-96:4 enantiomeric ratio). The control experiments indicated that o-hydroxyphenyl substituted p-quinone methides had a high possibility to transform into o-quinone methides in the presence of chiral phosphoric acid, and the formation of o-quinone methides might be a necessity for the reaction. This reaction will not only contribute to the research field of catalytic asymmetric transformations of p-quinone methides and o-quinone methides but also provide a useful method for the construction of enantioenriched triarylmethane frameworks.
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