Journal of Organic Chemistry p. 2576 - 2580 (1987)
Update date:2022-08-04
Topics:
Keinan, Ehud
Perez, Daniel
A novel reducing system comprised of phenylsilane and catalytic amounts of Mo(CO)6 in refluxing THF efficiently effects conjugate reduction of Michael acceptors, including α,β-unsaturated ketones, carboxylic acids, carboxylic esters, amides, and nitriles.The process involves molybdenum-catalyzed hydrosilation, followed by hydrolysis of the intermediate silyl enol ether.Hydride is regioselectively transferred from the hydridosilane to the β-carbon of the substrate, and a proton from water is incorporated into the α-carbon.
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Doi:10.1021/jo00388a034
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