Highly regio- and stereoselective hydrosilylation of β-fluoroalkylated α,β-unsaturated ketones

•Co2(CO)8-catalyzed hydrosilylation of β-fluoroalkylated α,β-unsaturated ketones gave the corresponding silyl enol ethers.•Various fluoroalkylated silyl enol ethers could be synthesized under the very mild conditions.•Thus-obtained silyl enol ethers could participate in the TiCl4-mediated stereosele...

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Bibliographic Details
Published in:Journal of fluorine chemistry 2015-05, Vol.173, p.69-76
Main Authors: Ikeda, Natsumi, Konno, Tsutomu
Format: Article
Language:English
Subjects:
Aldol reaction
Dicobalt octacarbonyl
Hydrosilylation
Regioselective
Stereoselective
β-Fluoroalkylated α,β-unsaturated ketones
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Summary:•Co2(CO)8-catalyzed hydrosilylation of β-fluoroalkylated α,β-unsaturated ketones gave the corresponding silyl enol ethers.•Various fluoroalkylated silyl enol ethers could be synthesized under the very mild conditions.•Thus-obtained silyl enol ethers could participate in the TiCl4-mediated stereoselective aldol reaction.•Hydrosilylation and the following aldol reaction could be performed consecutively in an one-pot. Treatment of β-fluoroalkylated α,β-unsaturated ketones with 10.2equiv of triethylsilane in the presence of 3mol% of Co2(CO)8 in dichloroethane at the reflux temperature for 4h gave 1,4-hydrosilylated adducts in a highly regio- and stereoselective manner. Thus-obtained silyl enol ethers underwent a smooth Mukaiyama aldol reaction with benzaldehyde in the presence of 1.2equiv of TiCl4 in CH2Cl2 at −78°C for 1h, affording the corresponding α-(2,2,2-trifluoroethyl)-β-hydroxy ketones with high syn stereoselectivity in good yields.
ISSN:0022-1139
1873-3328
DOI:10.1016/j.jfluchem.2015.02.010