A Novel One-Step Approach for the Preparation of alpha-Amino Acids, alpha-Amino Amides, and Dipeptides from Azetidine-2,3-Diones

Benito Alcaide; Pedro Almendros; Cristina Aragoncillo

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A Novel One-Step Approach for the Preparation of alpha-Amino Acids, alpha-Amino Amides, and Dipeptides from Azetidine-2,3-Diones

机译：从氮杂环丁烷-2,3-离子的制备α-氨基酸，α-氨基酰胺和二肽的一种新颖的一步方法

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摘要

A remarkable reaction of azetidine-2,3-diones with primary as well as secondary amines, and water is presented. Simply by varying the nucleophile, an unprecedented one-step synthesis of alpha-amino acids, alpha-amino amides, and dipeptides, was developed in both the racemic and optically pure forms. The current mechanistic hypothesis invokes a concerted process involving CO extrusion. However, a stepwise pathway can also account for these novel transformations.

机译：介绍了氮杂环丁烷2,3-二酮与伯胺和仲胺以及水的显着反应。只需通过改变亲核试剂，就可以以外消旋和光学纯净形式开发出前所未有的一步合成α-氨基酸，α-氨基酰胺和二肽的方法。当前的机械假设引发了涉及CO挤出的协调过程。但是，逐步途径也可以解释这些新颖的转化。

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《Chemistry: A European journal》 |2002年第16期|共7页
作者
Benito Alcaide; Pedro Almendros; Cristina Aragoncillo;
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原文格式 PDF
正文语种 eng
中图分类化学;应用化学;
关键词
amino acids; symmetric synthesis; cleavage reactions; beta-lactams; peptides;

机译：氨基酸对称合成裂解反应β-内酰胺肽;

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1. A Novel One-Step Approach for the Preparation of alpha-Amino Acids, alpha-Amino Amides, and Dipeptides from Azetidine-2,3-Diones [J] . Benito Alcaide, Pedro Almendros, Cristina Aragoncillo Chemistry: A European journal . 2002,第16期

机译：从氮杂环丁烷-2,3-离子的制备α-氨基酸，α-氨基酰胺和二肽的一种新颖的一步方法
2. Ecological Base-Conditioned Preparation of Dipeptides Using Unprotected alpha-Amino Acids Containing Hydrophilic Side Chains [J] . Ezawa Tetsuya, Jung Seunghee, Kawashima Yuya, Bulletin of the Chemical Society of Japan . 2017,第6期

机译：使用含有亲水侧链的未受保护的α-氨基酸的二肽的生态基础条件制备
3. DIMETHYLDICHLOROSILANE - AN EFFECTIVE REAGENT FOR ONE-STEP SYNTHESIS OF alpha-AMINO ACID AMIDES [J] . Balaev A. N., Osipov V. N., Okhmanovich K. A., Pharmaceutical Chemistry Journal . 2015,第5期

机译：二甲基氯硅烷-一种一步法合成α-氨基酸的有效试剂
4. From alpha-amino acids to enantiopure gamma-and omega-amino acids with proteinogenic side chains [C] . Vassilios Lokas, Caterina Noula, George Kokotos European Peptide Symposium . 2002

机译：用α-氨基酸与蛋白质侧链对γ-和ω-氨基酸进行对γ-和ω-氨基酸
5. ASYMMETRIC SYNTHESES OF ALPHA-AMINO ACIDS AND ALPHA-AMINO ALDEHYDES VIA ELECTROPHILIC SUBSTITUTION OF CHIRAL LITHIOCARBANIONS. [D] . DAVENPORT, KENNETH GERALD. 1982

机译：通过手性锂碳的亲电取代反应合成α-氨基酸和α-氨基醛。
6. Effect of acidic (dicarboxylic) alpha-amino acids on uptake of L-histidine by intestinal mucosa testis spleen and kidney in vitro: a comparison with effect in brain. [O] . K D Neame 1965

机译：酸性（二羧酸）α-氨基酸对肠粘膜睾丸脾脏和肾脏摄取L-组氨酸的影响：与脑内作用的比较。
7. The reactions of alpha-amino acids and alpha-amino acid esters with high valent transition metal halides: synthesis of coordination complexes, activation processes and stabilization of alpha-ammonium acylchloride cations [O] . Biancalana, L., Bortoluzzi, M., Ferretti, E., 2017

机译：α-氨基酸和α-氨基酸酯与高价过渡金属卤化物的反应：配位化合物的合成，活化过程和α-铵氯酰阳离子的稳定化

A Novel One-Step Approach for the Preparation of alpha-Amino Acids, alpha-Amino Amides, and Dipeptides from Azetidine-2,3-Diones

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