期刊
CHINESE JOURNAL OF CHEMISTRY
卷 36, 期 10, 页码 925-928出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/cjoc.201800319
关键词
asymmetric catalysis; dearomatization; fluorination; organocatalysis; phase-transfer catalysis; tryptophol
资金
- National Key Research and Development Program of China [2016YFA0202900]
- National Basic Research Program of China [2015CB856600]
- NSFC [21332009, 21572252]
- Program of Shanghai Subject Chief Scientist [16XD1404300]
- Strategic Priority Research Program [XDB20000000]
- Key Research Program of Frontier Sciences of Chinese Academy of Sciences [QYZDYSSW-SLH012]
An asymmetric fluorinative dearomatization reaction of tryptophol derivatives was developed via chiral anion phase-transfer catalysis. Various fluorinated furoindolines were obtained in moderate to excellent yields and enantioselectivity in the presence of Selectfluor. The preliminary mechanistic studies suggested the existence of an in situ formed tryptophol boronic ester plays a critical role in determining the enantioselectivity. This method features the facile introduction of a fluorine atom in a highly enantioselective manner and construction of two contiguous quaternary stereogenic centers.
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