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Issue 83, 2018

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

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Abstract

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.

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

Supplementary files

Article information


Submitted
03 Aug 2018
Accepted
24 Sep 2018
First published
24 Sep 2018

Chem. Commun., 2018,54, 11809-11812
Article type
Communication

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

T. Neves-Garcia, A. Vélez, J. M. Martínez-Ilarduya and P. Espinet, Chem. Commun., 2018, 54, 11809 DOI: 10.1039/C8CC06358C

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