Journal
JOURNAL OF FLUORINE CHEMISTRY
Volume 152, Issue -, Pages 46-50Publisher
ELSEVIER SCIENCE SA
DOI: 10.1016/j.jfluchem.2013.01.032
Keywords
Trifluoromethylation; Aldehyde; Chiral catalysis; Enantioselective; Phase-transfer catalysts
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Funding
- MEXT (Ministry of Education, Culture, Sports, Science and Technology) [24105513, 2304]
- Technology Agency (ACT-C: Creation of Advanced Catalytic Transformation for the Sustainable Manufacturing at Low Energy, Low Environmental Load)
- TOSOH F-TECH, INC.
- Grants-in-Aid for Scientific Research [10J08891, 24105513] Funding Source: KAKEN
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The catalytic enantioselective trifluoromethylation reaction of aromatic aldehydes using the Ruppert-Prakash reagent (Me3SiCF3) has been disclosed, with an operationally simple procedure, based on the combination of sterically demanding cinchona alkaloid-derived phase-transfer catalyst 3b with tetramethylammonium fluoride (TMAF). Our methodology provides medicinally important alpha-trifluoromethyl alcohols with high chemical yields and moderate to good enantioselectivities (50-70% ee). (c) 2013 Elsevier B.V. All rights reserved.
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