Issue 28, 2008

Unexpected effect of the fluorine atom on the optimal ligand-to-palladium ratio in the enantioselective Pd-catalyzed allylation reaction of fluorinated enol carbonates

Abstract

The enantioselective Pd-catalyzed allylation reaction of fluorinated allyl enol carbonates is presented; a key feature of this transformation is the important effect of the ligand-to-palladium ratio on the enantioselectivity of the α-fluoroketones, since using a ligand excess (L/Pd ratio = 1.25 : 1) led to moderate results (30–76% ee), while using a L/Pd ratio <1 : 1.67 (to as low as 1 : 4) allowed the desired products to be obtained with high enantiopurity (up to 94% ee).

Graphical abstract: Unexpected effect of the fluorine atom on the optimal ligand-to-palladium ratio in the enantioselective Pd-catalyzed allylation reaction of fluorinated enol carbonates

Supplementary files

Article information

Article type
Communication
Submitted
25 Feb 2008
Accepted
15 Apr 2008
First published
15 May 2008

Chem. Commun., 2008, 3251-3253

Unexpected effect of the fluorine atom on the optimal ligand-to-palladium ratio in the enantioselective Pd-catalyzed allylation reaction of fluorinated enol carbonates

É. Bélanger, C. Houzé, N. Guimond, K. Cantin and J. Paquin, Chem. Commun., 2008, 3251 DOI: 10.1039/B803097A

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