Preparation method of alpha,beta-epoxy amide compounds

Abstract

The invention discloses a preparation method of alpha,beta-epoxy amide compounds, which comprises the following steps: in the presence of an oxidizer and a catalyst, carrying out epoxidation on the alpha,beta-unsaturated amide compounds disclosed as Formula (IV) to obtain the alpha,beta-epoxy amide compounds, wherein the catalyst is hydrate of levulose-derived chiral ketone disclosed as Formula (I) or levulose-derived chiral ketone disclosed as Formula (II). The alpha,beta-unsaturated amide compounds used as the raw material is directly subjected to asymmetric epoxidation in the presence of the oxidizer by using the cheap and accessible hydrate of the levulose-derived chiral ketone disclosed as Formula (I) or levulose-derived chiral ketone disclosed as Formula (II) as the catalyst. The method has the advantage of mild reaction conditions, is simple to operate, and can obtain the photoactive alpha,beta-epoxy amide compounds through the simple column chromatography after-treatment step; and the maximum enantiomeric excess value (ee value) is up to 97%. Since the catalyst and operational method are simple, the invention has certain potential industrial application value.

Description

technical field [0001] The invention relates to a preparation method of α, β-epoxyamide compounds. Background technique [0002] The epoxy compound of α,β-unsaturated amides can be used as a good intermediate in organic synthesis, and it can selectively ring-open to generate α-hydroxyamides or β-hydroxyamides. The synthesis method of α, β-epoxy amides has the sulfur ylide reaction ((a) Aggarwal, V.K.; Hynd, G.; Picoul, W.; Vasse, J.-L.J.Am) reported by Aggarwal using chiral sulfur reagent .Chem.Soc.2002,124,9964.(b)Aggarwal,V.K.;Winn,C.L.Acc.Chem.Res.2004,37,611.(c)Aggarwal,V.K.;Charmant,J.P.H.;Fuentes,D.;Harvey,J.N. ;Hynd,G.;Ohara,D.;Picoul,W.;Robiette,R.;Smith,C.;Vasse,J.-L.;Winn,C.L.J.Am.Chem.Soc.2006,128,2105.) . In 2002, Shibasaki et al. used metals such as Gd, Sm and BINOL to jointly catalyze the asymmetric epoxidation reaction of α, β-epoxyamide compounds. This is the first case of catalyzed asymmetric epoxy amide compounds. Chemical reactions (T. Nemoto, H. Kakai...

AI Technical Summary

Problems solved by technology

[0003] In summary, the existing methods for synthesizing epoxides of α,β-unsaturated amides mainly rely on chiral prosthetic group-induced synthesis or some expensive metal-catalyzed asymmetric reactions, and cannot be prepared in large quantities

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