Amino group-containing chiral ionic liquid and its prepn process and application

Abstract

The present invention relates to amino group-containing chiral ionic liquid and its preparation process and application in organic asymmetrical catalytic Michael reaction. The chiral ionic liquid has the general expression of A+B-, A+ is shown, and B- is halogen ion or other negative ions as shown. The preparation process includes the following steps: the reflux reaction between amino acid derived halogenated fatty amine haloid and substituting imidazole in organic solvent, and the neutralization of the reacted liquid to obtain the product. The chiral ionic liquid with connected imidazole cycle possessing excellent stereo steric hindrance effect has excellent chiral catalytic performance on Michael reaction except its application as common ionic liquid.

Description

(1) Technical field [0001] The invention relates to an amino group-containing chiral ionic liquid, a preparation method and an application thereof. (2) Background technology [0002] Asymmetric synthesis has become an important research direction of chemistry in the 21st century and an indispensable part of the fields of organic synthetic chemistry, biochemistry, medicinal chemistry and pesticide chemistry. Usually, asymmetric synthesis reactions are realized by using chiral auxiliary agents, chiral reagents and chiral catalysts. Catalytic asymmetric synthesis is the most ideal asymmetric synthesis method, it only uses a small amount of chiral catalyst to obtain a large number of chiral products. Chiral catalysts can be divided into chiral organic complex metal catalysts, enzymes and chiral organic molecular catalysts. Chiral organic molecular catalysts are increasingly valued because they are environmentally friendly and do not use expensive transition metals and chiral li...

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Problems solved by technology

In 2000, Hanessian et al. discovered that L-proline can chirally catalyze the asymmetric Michael reaction between nitroalkyl and enone (Organic Lett., 2000, 2, 2975). Soon after, Barbas et al. used (5) in the asymmetric The Michael addition reaction has a good catalytic effect, and the ee value of the product can reach 91% (Tetrahedron Lett., 2001, 42, 4441). At the same time, (6) asymmetric Michael reaction of aldehydes and nitrovinyl compounds was also reported , the product yield reaches 96%, the diastereomer ratio is 98:2, and the ee value can reach 78%, but it is difficult to recover and apply the catalyst (Organic Lett., 2001, 3, 3737)

Especially with proline as organic small molecule catalyst, Aldol reaction in ionic liquid can obtain 71% ee value, but the yield and ee value begin to decline after repeating mechanically four times (Tetrahedron Lett.2002, 43, 8741)

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