Highly enantioselective addition of dimethylzinc to fluorinated alkyl ketones, and the mechanism behind it

Chiral-diamine catalyzed addition of ZnMe2 to PhC(O)CF2X (in dichloromethane at -30 °C) affords fluorinated alkyl tertiary alcohols in high yield (quantitative for X = H, F, Cl; 84% for X = CF3) and up to 99% ee. These conditions are similarly very efficient for other various ArC(O)CF3 molecules. A...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2018-10, Vol.54 (83), p.11809-11812
Main Authors: Neves-Garcia, Tomaz, Vélez, Andrea, Martínez-Ilarduya, Jesús M, Espinet, Pablo
Format: Article
Language:English
Subjects:
Alcohols
Dichloromethane
Enantiomers
Fluorination
Ketones
NMR
Nuclear magnetic resonance
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Summary:Chiral-diamine catalyzed addition of ZnMe2 to PhC(O)CF2X (in dichloromethane at -30 °C) affords fluorinated alkyl tertiary alcohols in high yield (quantitative for X = H, F, Cl; 84% for X = CF3) and up to 99% ee. These conditions are similarly very efficient for other various ArC(O)CF3 molecules. A fine analysis of the results can be performed based on a double-cycle mechanism.
ISSN:1359-7345
1364-548X
DOI:10.1039/c8cc06358c