期刊
ASIAN JOURNAL OF ORGANIC CHEMISTRY
卷 3, 期 4, 页码 449-452出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ajoc.201402016
关键词
cinchona alkaloids; efavirenz; organocatalysis; tetramethylammonium fluoride; trifluoromethylation
资金
- Japan Science and Technology Agency (JST)
- MEXT Japan [24105513, 25288045]
- JST, Exploratory Research [25670055]
- Grants-in-Aid for Scientific Research [25670055, 24105513, 25288045] Funding Source: KAKEN
We demonstrate a metal-free catalytic process for the synthesis of anti-HIV drug efavirenz in 99% ee, which was achieved by an organocatalyzed enantioselective trifluoromethylation with Me3SiCF3 as a key reaction. The combination of cinchona alkaloid-derived phase-transfer catalysts modified with long chain ethers and tetramethylammonium fluoride enables the enantioselective trifluoromethylation of 1-(5-chloro-2-nitrophenyl)-3-cyclopropylprop-2-yn-1-one to be improved, and provides a desired (S)-trifluoromethyl carbinol, which is a two-step key precursor for the synthesis of efavirenz, in up to 80% ee. As our method is a metal-free process, it would provide an alternative industrial manufacturing process for efavirenz.
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