Efficient one-pot synthesis of enantiomerically pure N-protected-alpha-substituted piperazines from readily available alpha-amino acids

Jida Mouhamad; Ballet Steven

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Efficient one-pot synthesis of enantiomerically pure N-protected-alpha-substituted piperazines from readily available alpha-amino acids

机译：从易于α-氨基酸的易于α-氨基酸的高效单壶合成对映体纯N保护 - α-取代的哌嗪

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A new pathway towards enantiomerically pure 3-substituted piperazines, bearing a benzyl protecting group, has been developed in good overall yields (83-92%), starting from commercially available N-protected amino acids. The methodology represents an efficient and simple one-pot procedure, employing a synthetic sequence consisting of an Ugi-4 component reaction, a Boc-deprotection, an intramolecular cyclisation reaction and a final reduction (UDCR). From the benzyl protected precursors, the 2-substituted piperazines bearing a Boc-protecting group could consequently also be obtained via a simple protection and deprotection step of the corresponding piperazines. The practical utility of this methodology was demonstrated for chiral drug synthesis.

机译：载有苄基保护基团的对映体纯3取代的哌嗪的新途径已经出于从市售的N-保护的氨基酸开始的良好总体产率（83-92％）。该方法代表了一种有效且简单的单罐方法，采用由Ugi-4组分反应，Boc-脱保护，分子内的环化反应和最终还原（UDCR）组成的合成序列。从苄基受保护的前体，也可以通过相应的哌嗪的简单保护和脱保护步骤来获得承载BOC保护基的2-取代的哌嗪。该方法的实用效用被证明了手性药物合成。

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《New Journal of Chemistry》 |2018年第3期|共5页
作者
Jida Mouhamad; Ballet Steven;
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Vrije Univ Brussel Dept Chem Res Grp Organ Chem Pl Laan 2 B-1000 Brussels Belgium;

Vrije Univ Brussel Dept Chem Res Grp Organ Chem Pl Laan 2 B-1000 Brussels Belgium;

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正文语种 eng
中图分类化学;
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1. Efficient one-pot synthesis of enantiomerically pure N-protected-alpha-substituted piperazines from readily available alpha-amino acids [J] . Jida Mouhamad, Ballet Steven New Journal of Chemistry . 2018,第3期

机译：从易于α-氨基酸的易于α-氨基酸的高效单壶合成对映体纯N保护 - α-取代的哌嗪
2. A convenient synthesis of enantiomerically pure alpha-isocyano esters and N-beta-Fmoc- amino alkyl isonitriles derived from alpha-amino acids employing PPh3/I-2 under mild conditions [J] . Santhosh L., Shekharappa, Krishnamurthy M., Indian Journal of Chemistry, Section B. Organic Including Medicinal . 2018,第9期

机译：在温和条件下衍生自α-氨基酸的对映体纯α-异氰酸酯和N-β-FMOC-氨基烷基异腈的合成
3. Preparation of Enantiomerically Pure Perfluorobutanesulfinamide and Its Application to the Asymmetric Synthesis of alpha-Amino Acids [J] . Wangweerawong Apiwat, Hummel Joshua R., Bergman Robert G., The Journal of Organic Chemistry . 2016,第4期

机译：对映体纯的全氟丁烷亚磺酰胺的制备及其在α-氨基酸不对称合成中的应用
4. Synthesis of enantiomerically pure cyclopropane analogues of proteinogenic amino acids using chiral HPLC [C] . Carlos Cativiela, Ana I.Jimenez, Gema Ballano, European Peptide Symposium . 2002

机译：手性HPLC的蛋白质氨基酸对映体纯环丙烷类似物的合成
5. The design and synthesis of novel chiral Z-nitrones with applications towards the syntheses of enantiomerically pure 4-hydroxy amino acids. [D] . Stanko, John August. 2009

机译：新型手性Z-硝酮的设计和合成及其对映体纯的4-羟基氨基酸的合成应用。
6. One-pot synthesis of enantiomerically pure N-protected allylic amines from N-protected α-amino esters [O] . Gastón Silveira-Dorta, Sergio J Álvarez-Méndez, Víctor S Martín, 2016

机译：从N保护的α-氨基酯一锅法合成对映体纯的N保护的烯丙基胺
7. Efficient access to enantiomerically pure cyclic alpha-amino esters through a lipase-catalyzed kinetic resolution [O] . Alatorre Santamaría, Sergio Andrés, Rodríguez Mata, María, Gotor Fernández, Vicente, 2008

机译：通过脂肪酶催化的动力学拆分有效地获得对映体纯的环状α-氨基酯

Efficient one-pot synthesis of enantiomerically pure N-protected-alpha-substituted piperazines from readily available alpha-amino acids

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