Asymmetrische katalysen: XLVI. Enantioselektive Hydrosilylierung von Ketonen mit [Rh(COD)Cl]2 und optisch aktiven Stickstoff-Liganden☆

Add time:08/18/2019    Source:sciencedirect.com

The synthesis and characterisation of 16 optically active nitrogen ligands, namely, pyridinethiazolidones, pyridinethiazolines, pyridinimidazolines, Schiff bases and bipyridines, are described. These ligands are used as cocatalysts together with the procatalyst [Rh(COD)Cl]2 in the catalytic hydrosilylation of prochiral ketones with diphenylsilane. With these homogeneous in situ catalysts, optically active 1-phenylethanol is produced from acetophenone after hydrolysis of the silyl ether. The diastereomers of N-(1-phenylethyl)-2-(2-pyridinyl)-thiazolidine-4-one give opposite optical inductions. The best optical purity of 71.6% ee is obtained with a pinanyl-substituted bipyridine.

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