Journal
ORGANIC LETTERS
Volume 21, Issue 9, Pages 3387-3391Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.9b01131
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Funding
- JST ACT-C [JPMJCR12Z7]
- JSPS KAKENHI [26620078]
- Grants-in-Aid for Scientific Research [26620078] Funding Source: KAKEN
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Chiral C-2-symmetric phosphinic acids were designed based on sterically demanding and helical chiral perfluoroalkyl groups at the closest alpha-position advancing asymmetric reaction environment and catalytic activity. The perfluoroalkyl catalysts, [(CF3)(2)F-2] and [(C2F5)(2)F-2] phosphinic acids, were synthesized via a stereoselective addition/cyclization sequence of methyl phosphinate and deoxofluorination. These new classes of Bronsted acid catalysts were applied to an asymmetric Friedel-Crafts reaction to give up to 89% yield and 82% R-enantioselectivity, which is higher than those obtained with the parent phosphoric acid (42% and 55.5% S).
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