Catalyst for splitting racemic epoxyalkane and application thereof

Abstract

The invention relates to a catalyst for splitting racemic epoxyalkane. The catalyst is composed of nitrogen-containing organic alkali or quaternary ammonium salt, and Cr (Salen) [(R,R)/(S,S)-N,N'-Bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediamino chromium (III) chloride], the mole ratio of the organic alkali or quaternary ammonium salt to the Cr (Salen) is 0.1-10; in the process of carrying out asymmetric ring-opening splitting of the racemic epoxyalkane, the splitting conversion rate of the catalyst to epoxyalkane can be greater than 49%, and the ee value of a split product 1-azido-2-trialkyl siloxane can be over 90%. The catalyst mainly solves the problem that previous catalytic racemic epoxyalkane is low in asymmetric ring-opening reaction activity, large in application amount of the catalyst and low in enantioselectivity, realizes the efficient splitting of racemic epoxyalkane, and can obtain high-purity chiral epoxyalkane and trialkyl siloxane.

Description

technical field [0001] The present invention relates to a kind of catalyst that is used for splitting racemic alkylene oxide, is made up of nitrogen-containing organic base or quaternary ammonium salt and Cr (Salen) specifically, and it is used for catalyzing asymmetric splitting racemic cycloalkylene oxide. Background technique [0002] Enantiomers of 1,2-aminoalcohols can not only be used as intermediates in the synthesis of various biologically important compounds, but also can be used as highly efficient and multifunctional precursors for asymmetric catalysis, so they are widely used in biopharmaceuticals and organic The field of synthesis is of great application value (Y.Shioiri, Y.Hamada, Heterocycles, 1988, 27, 1035; C.B.Barlow, S.T.Bukhari, R.D.Guthrie, A.M.Prior, Asymmetry in Carbohydrates, Dekker: New York, 1979, pp 81-99 ). The existing synthesis routes of amino alcohols largely rely on the reduction of chiral precursors or amino acids. Although this method can...

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Problems solved by technology

But this method needs special instrumentation-microwave synthesizer to assist to complete, and the enantioselectivity of the resolution product 1-azido-2-trimethylsiloxane obtained is only 90%

Choong-Eui Song's research group (C.E.Song et al., WO2002012171) selected ionic liquid as the solvent for the catalytic reaction. Although the catalyst was successfully reused, the amount of the catalyst was as high as 3% mol, which was still not ideal.

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