期刊
ADVANCED SYNTHESIS & CATALYSIS
卷 360, 期 12, 页码 2377-2381出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201800290
关键词
Cycloaddition; Organic Base; Base Catalysis; Oxidopyrylium Ylide; Alkenes
资金
- Japan Society for the Promotion of Science (JSPS) [JP15 K05497]
An efficient method for the preparation of a range of 8-oxabicyclo[3.2.1]octane derivatives including synthetic intermediates of natural products is described, in which triethylamine effectively catalyzes [5+2] cycloaddition reactions between oxidopyrylium ylides and alkenes. This method can be applied not only to intermolecular cycloadditions with various alkenes but also to intramolecular cycloadditions. The key finding is that the combined use of organic bases having appropriate basicity and oxidopyrylium ylide precursors bearing a suitable leaving group facilitates the base-assisted generation of oxidopyrylium ylides in a catalytic manner.
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