Synthesis of enantiomerically pure 2-(N-aryl, N-alkyl-aminomethyl)aziridines: a new class of ligands for highly enantioselective asymmetric synthesis

Q2 Chemistry

Tetrahedron, asymmetry Pub Date : 2017-12-15 DOI:10.1016/j.tetasy.2017.10.018

Szymon Jarzyński, Stanisław Leśniak, Michał Rachwalski

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引用次数: 7

Abstract

A simple and effective synthesis of enantiomerically pure 2-(N-aryl-, N-alkyl-aminomethyl)aziridines from (2S)-N-tritylaziridine-2-carboxylic acid methyl ester has been developed. Treating of this key ester with several primary and secondary amines in the presence of AlMe₃ provided the corresponding chiral N-trityl-2-carboxamides, and their reduction performed with different reagents resulted in the formation of the expected 2-(aminomethyl)aziridines. The choice of reaction conditions allows to either keep or leave the trityl substituent in the product. Such 2-(aminoalkyl)aziridines have shown very high catalytic efficiency in the asymmetric arylation of aldehydes and in other testing asymmetric reactions. On the other hand, homochiral N-trityl-2-carboxamides are interesting building blocks for the synthesis of various biologically active compounds.

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对映纯2-(n -芳基，n -烷基-氨基甲基)叠氮嘧啶的合成:一类用于高对映选择性不对称合成的新配体

以(2S)- n -三烷基叠氮吡啶-2-羧酸甲酯为原料，简单有效地合成了对映体纯的2-(n -芳基，n -烷基-氨基甲基)叠氮吡啶。在AlMe3的存在下，用几种伯胺和仲胺处理该关键酯，得到了相应的手性n -三烷基-2-羧酰胺，用不同的试剂还原它们，形成了预期的2-(氨基甲基)亚氮嘧啶。反应条件的选择允许产物中保留或留下三甲基取代基。这种2-(氨基烷基)偶氮吡啶在醛的不对称芳基化反应和其他测试中的不对称反应中显示出很高的催化效率。另一方面，同手性n -三烷基-2-羧酰胺是合成各种生物活性化合物的有趣的基石。

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来源期刊

Tetrahedron, asymmetry 化学-无机化学与核化学

CiteScore

4.70

自引率

0.00%

发文量

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.