Derivative containing halogen light active oxazolidinone and preparation method thereof

A technology of substrates and compounds, applied in organic chemistry and other fields
CN103073516BInactive Publication Date: 2014-08-13INST OF CHEM CHINESE ACAD OF SCI
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Patent Information

Authority / Receiving Office
CN · China
Patent Type
Patents(China)
Current Assignee / Owner
INST OF CHEM CHINESE ACAD OF SCI
Publication Date
2014-08-13
Estimated Expiration
Not applicable · inactive patent

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Abstract

The invention discloses a halogen-containing optically active oxazolidinone derivative and a preparation method therefor. The structural formula of the compound is shown as formula I. In the present invention, N-bromosuccinimide is used as a bromine source, and a complex of a chiral phosphine ligand and a Lewis acid is used as a catalyst to catalyze olefin substrates with different structures in an asymmetric bromine amine cyclization reaction; the optically active oxazolidinone derivative is synthetically prepared through a simple post-processing step of column chromatography. An enantiomer excess value (ee value) can reach up to 97%. The reaction can be scaled up to gram level and the ee value of the product after recrystallization can reach 99%, therefore the reaction has a potential industrial application value. Furthermore, the reaction product can be further derived into various useful compounds so as to achieve the application values of the product.
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Description

technical field

[0001] The invention relates to a halogen-containing photoactive oxazolinone derivative and a preparation method thereof. Background technique

[0002] The halogenation reaction of alkenes is one of the most important elementary reactions in synthetic chemistry, which provides a very simple and effective way for the functionalization of alkenes. The asymmetric halogenation reaction of alkenes can introduce two chiral heteroatoms on the double bond at the same time, and the halogen atoms in the product can undergo various transformations, such as stereoselective substitution reactions, etc., thus becoming an important in organic synthesis. synthon. Due to its great importance, the asymmetric halogenation of alkenes has aroused widespread interest among chemists, and great progress has been made in recent years. At present, there are many reports on chiral amine-catalyzed systems, but most of them are limited to asymmetric halide lactonization. There are als...

Claims

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