期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 57, 期 14, 页码 3806-3809出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201800567
关键词
asymmetric catalysis; indole alkaloids; Michael addition; oxindoles; synthetic methods
资金
- Natural Science and Basic Research Plan of Shaanxi Province [2014JZ2-001]
- Open Fund of State Key Laboratory of Bioorganic & Natural Products
- Scientific Research Foundation of Northwest AF University
- National Natural Science Foundation of China [21672171, 21722206]
A highly enantioselective tandem Michael addition of tryptamine-derived oxindoles to alkynones was developed by taking advantage of a chiral N,N-dioxide Sc(OTf)(3) catalyst. The reaction enables the facile preparation of enantioenriched spiro[pyrrolidine-3,3-oxindole] compounds, which provides a novel strategy for the synthesis of monoterpenoid indole alkaloids. As a demonstration, the asymmetric synthesis of strychnos alkaloids [(-)-tubifoline, (-)-tubifolidine, (-)-dehydrotubifoline] was achieved in 10-11 steps.
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