期刊
ORGANIC LETTERS
卷 18, 期 14, 页码 3442-3445出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.6b01623
关键词
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资金
- Department of Science and Technology, DST [SB/FT/CS-006/2013]
- Council of Scientific and Industrial Research, CSIR [02(0219)/14/EMR-II]
- DST, India
- Federal Ministry of Science, Research and Economy (BMWFW) of Austria [INT/AUA/BMWF/P-26/2015]
A novel palladium-catalyzed hydration-olefin insertion cascade assisted by internal nucleophiles was developed for the synthesis of biologically significant 2,3-dihydro-1H-inden-1-ones under mild conditions. A detailed mechanistic study revealed that the assistance of the internal nucleophiles is crucial to trigger the cascade reaction via nucleopalladation of the alkyne moiety. The overall reaction is equivalent to regioselective hydration of alkynes followed by intramolecular Michael addition. This highly efficient and 100% atom-economical domino sequence afforded cis-2,3-disubstituted 2,3-dihydro-1H-inden-1-ones in excellent yields (up to 99%) with complete diastereoselectivity.
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