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Synfacts 2016; 12(08): 0839
DOI: 10.1055/s-0035-1562396
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Enantioselective Addition of Organoboron Reagents to Fluoroketones

Contributor(s):
Paul Knochel
,
Dorothée Ziegler
Lee K, Silverio DL, Torker S, Robbins DW, Haeffner F, van der Mei FW, Hoveyda AH * Boston College, Chestnut Hill, USA
Catalytic Enantioselective Addition of Organoboron Reagents to Fluoroketones Controlled by Electrostatic Interactions.

Nature Chem. 2016;
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Publication History

Publication Date:
19 July 2016 (online)

 
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Key words

organoboron reagents - fluoroketones - enantioselectivity

Significance

Hoveyda and co-workers have developed an efficient catalytic method for the addition of allyl and allenyl organoboron reagents to fluoroketones, leading to trifluoromethyl-substituted tertiary alcohols in up to 98% yield.


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Comment

The versatility of the presented method is illustrated in an enantioselective route to the antiparasitic drug fluralaner (Bravecto, Merck).


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