缬氨酸甲酯Betti反应中的立体选择

Q2 Chemistry
Maria Annunziata M. Capozzi , Cosimo Cardellicchio
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引用次数: 12

摘要

2-萘酚、苯甲醛和(S)-胺的多组分Betti反应通常产生具有两个立体中心的高价值氨基苯萘酚,当(S)-缬氨酸甲酯作为通常反应方案中的胺时,生成完全外消旋的产物。这一缺陷的原因似乎在文献中被忽视了,我们对此进行了调查。结果,建立了新的反应条件,能够产生预期的有用产物,具有两个完全分解的立体中心。此外,当对苯环上取代基的影响进行初步研究时,我们发现4-氟和4-氯苯甲醛在原始反应方案中也得到了立体异构纯化合物。
本文章由计算机程序翻译,如有差异,请以英文原文为准。

Stereoselection in the Betti reaction of valine methyl esters

Stereoselection in the Betti reaction of valine methyl esters

The multi-component Betti reaction of 2-naphthol, benzaldehyde and (S)-amines, that usually provides highly valuable aminobenzylnaphthol bearing two stereogenic centers, yielded a completely racemic product, when (S)-valine methyl ester was employed as the amine in the usual reaction protocol. The cause of this drawback, that appears to be overlooked in the literature, was investigated. As a result, new reaction conditions were set up, that were able to yield the expected useful product, having two fully resolved stereogenic centers. Furthermore, when the effect of substituents on the phenyl ring was preliminarily studied, we found that 4-fluoro- and 4-chlorobenzaldeyde gave stereoisomerically pure compounds also in the original reaction protocol.

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来源期刊
Tetrahedron, asymmetry
Tetrahedron, asymmetry 化学-无机化学与核化学
CiteScore
4.70
自引率
0.00%
发文量
0
审稿时长
1 months
期刊介绍: Cessation. Tetrahedron: Asymmetry presents experimental or theoretical research results of outstanding significance and timeliness on asymmetry in organic, inorganic, organometallic and physical chemistry, as well as its application to related disciplines, especially bio-organic chemistry. The journal publishes critical reviews, original research articles and preliminary communications dealing with all aspects of the chemical, physical and theoretical properties of non-racemic organic and inorganic materials and processes. Topics relevant to the journal include: the physico-chemical and biological properties of enantiomers; strategies and methodologies of asymmetric synthesis; resolution; chirality recognition and enhancement; analytical techniques for assessing enantiomeric purity and the unambiguous determination of absolute configuration; and molecular graphics and modelling methods for interpreting and predicting asymmetric phenomena. Papers describing the synthesis or properties of non-racemic molecules will be required to include a separate statement in the form of a Stereochemistry Abstract, for publication in the same issue, of the criteria used for the assignment of configuration and enantiomeric purity.
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