Diboron glycol ester as well as preparation method, intermediate and application thereof

A biboronic acid glycol ester and halogen technology, applied in the field of biboronic acid glycol ester, can solve the problems of single structure of biboronic acid glycol ester and the like
CN111440205AActive Publication Date: 2020-07-24宁波赜军医药科技有限公司
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Patent Information

Authority / Receiving Office
CN · China
Current Assignee / Owner
宁波赜军医药科技有限公司
Publication Date
2020-07-24

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Abstract

The invention discloses diboron glycol ester as well as a preparation method, an intermediate and application thereof. The diboron glycol ester can be used for inducing reductive coupling reaction with imine as a substrate, and the substrate can be obtained by reaction of aldehyde and ammonia and is very easy to obtain and quite low in cost. The product can be separated from a reaction system onlyby acid-base operation without column chromatography purification, and the post-treatment mode is convenient and easy to operate. The yield of the obtained product is high, and protective group operation is not needed. The diboron glycol ester has chirality, the stereoselectivity of the reductive coupling reaction is generally excellent, and 99% ee chiral diamine can be obtained only through simple recrystallization. The diboron glycol ester can be obtained by reacting diol with diboron glycol ester, the diol is convenient to prepare and easy to amplify, the diol can be recycled from a reaction solution through simple acid-base operation, the recovery rate reaches 95%, and the preparation cost is further saved.
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Description

technical field

[0001] The present invention relates to a diboronic acid glycol ester, its preparation method, its intermediate and its application. Background technique

[0002] Biboronic acid glycol ester has the advantages of non-toxicity, stability, easy operation, etc., and has a wide range of uses in organic synthesis. According to different sources of diols, it can be divided into achiral diboronic acid diol ester and chiral diboronic acid diol ester. Among them, achiral diboronic acid glycol ester was widely used in Miyaura coupling reaction to prepare organoboronate compounds (Org. Synth. 2000, 77, 176-185). With the development of organic chemistry in recent years, it has also been gradually applied to the addition of alkenes, alkynes, aldehydes (ketones), imines and other compounds and the C-H boron substitution of aromatic compounds (Chem.Rev.2016, 116,9091). Compared with achiral diboronic acid diol esters, due to the limited sources of chiral diols and the g...

Claims

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