Journal
JOURNAL OF FLUORINE CHEMISTRY
Volume 171, Issue -, Pages 46-55Publisher
ELSEVIER SCIENCE SA
DOI: 10.1016/j.jfluchem.2014.10.002
Keywords
Trifluoromethyl; Quaternary carbon; Allylation; Asymmetric; Nucleophile
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Funding
- National Basic Research Program of China (973 Program) [2012CB821600]
- National Natural Science Foundation of China [21032006, 21172241, 21421002]
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A new development in the palladium-catalyzed allylation reaction of trifluoromethylated ketene aminoacetals was reported. These nucleophilic reagents were prepared by adding aminoalcohols to methyl 3,3,3-trifluoro-2-trifluoromethylpropanoate. The asymmetric version of the allylation reaction was investigated using chiral oxazolidine-based starting materials or chiral palladium catalysts. Asymmetric allylic alkylation was carried out with up to 74% ee using a chiral catalyst. However, no improvement was observed using double stereodifferentiation. These results provided a novel access for trifluoromethylated all-carbon quaternary carbon centers. (C) 2014 Elsevier B.V. All rights reserved.
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