Enantioselective synthesis of 1,2,5,6-tetrahydropyridines (THPs) via proline-catalyzed direct Mannich-cyclization/domino oxidation-reduction sequence: application for medicinally important N-heterocycles

Ramaraju Panduga; Mir Nisar A.; Singh Deepika; Kumar Indresh

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Enantioselective synthesis of 1,2,5,6-tetrahydropyridines (THPs) via proline-catalyzed direct Mannich-cyclization/domino oxidation-reduction sequence: application for medicinally important N-heterocycles

机译：通过脯氨酸催化的直接曼尼希环化/多米诺氧化还原序列对映选择性合成1,2,5,6-四氢吡啶（THP）：在医学上很重要的N-杂环化合物的应用

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An enantioselective multi-component synthesis of 1,2,5,6-tetrahydropyridines (THPs) has been developed through a one-pot domino-process. This transformation proceeds through proline-catalyzed direct Mannich reaction-cyclization of glutaraldehyde with in situ generated imines, followed by site-selective oxidation-reduction sequence under mild conditions. Chiral 1,2,5,6-THPs are obtained in good to high yields (up to 80%) and with the excellent enantioselectivity (up to 98 : 2 er). The usefulness of this operationally simple method is also shown to synthesize other medicinally important nitrogen-heterocycles.

机译：通过一锅多米诺法开发了一种对映选择性的多组分合成1,2,5,6-四氢吡啶（THPs）的方法。这种转化通过脯氨酸催化戊二醛与原位生成的亚胺的直接曼尼希反应环化进行，然后在温和条件下进行位点选择性氧化还原序列。获得的手性1,2,5,6-THP产率高至高（高达80％），并且具有出色的对映选择性（高达98：2 er）。还显示了这种操作简单的方法的有用性，可以合成其他医学上重要的氮杂环。

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《RSC Advances》 |2016年第65期|共11页
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Ramaraju Panduga; Mir Nisar A.; Singh Deepika; Kumar Indresh;
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1. Enantioselective synthesis of 1,2,5,6-tetrahydropyridines (THPs) via proline-catalyzed direct Mannich-cyclization/domino oxidation-reduction sequence: application for medicinally important N-heterocycles [J] . Ramaraju Panduga, Mir Nisar A., Singh Deepika, RSC Advances . 2016,第65期

机译：通过脯氨酸催化的直接曼尼希环化/多米诺氧化还原序列对映选择性合成1,2,5,6-四氢吡啶（THP）：在医学上很重要的N-杂环化合物的应用
2. Facile domino reactions in the statistically controlled product- and stereoselective synthesis of densely functionalized ds-1,4-cyclohexa-1,4-dienes and trans,trans-trisubstituted-1,2,5,6-tetrahydropyridines [J] . Palani Sokkan Harikrishnan, Stephen Michael Rajesh, Subbu Perumal Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry . 2012,第30期

机译：统计学上受控的稠密官能化ds-1,4-环己-1,4-二烯和反式，反式-三取代-1,2,5,6-四氢吡啶的产物和立体选择性合成中的轻松多米诺反应
3. An enantioselective organocatalyzed aza-MBH domino process: application to the facile synthesis of tetrahydropyridines [J] . Shinobu Takizawa, Naohito Inoue, Hiroaki Sasai Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry . 2011,第3期

机译：对映选择性的有机氮杂-MBH多米诺骨牌工艺：在四氢吡啶的简便合成中的应用
4. Part I. Asymmetric organocatalysis: (1) Direct enantioselective organocatalytic hydroxymethylation of aldehydes catalyzed by alpha,alpha-diphenylprolinol trimethylsilyl ether: Application in the formal synthesis of (-)-Rasfonin; (2) Synthesis of a novel bicyclic secondary amine organocatalyst: Application to the direct enantioselective organocatalytic hydroxymethylation of aldehydes. Part II. Asymmetric synthesis of bicyclic analogues of the anti-osteoporotic drug risedronate. [D] . Miller, John Robert. 2010

机译：第一部分，不对称有机催化：（1）α，α-二苯基脯氨醇三甲基甲硅烷基醚催化的醛的直接对映选择性有机催化羟甲基化：在（-）-Rasfonin的正式合成中的应用；（2）新型双环仲胺有机催化剂的合成：应用于醛的直接对映选择性有机催化羟甲基化。第二部分抗骨质疏松药物Risedronate的双环类似物的不对称合成。
5. Enantioselective Synthesis of α-Methylene-β-hydroxy Carboxylic Acid Derivatives via a Diastereoselective Aldol-β-Elimination Sequence: Application to the C(15)–C(21) Fragment of Tedanolide C [O] . Roland Barth, William R. Roush -1

机译：经由非对映选择性醛醇-β-消除序列的对映选择性合成α亚甲基β羟基羧酸衍生物：应用到C（15）-C（21）Tedanolide的C片段
6. Sulfoxide-directed enantioselective synthesis of functionalized tetrahydropyridines [O] . Fernández de la Pradilla Roberto, Simal Carmen, Bates Robert H., 2014

机译：亚砜定向对映选择性合成功能化的四氢吡啶

Enantioselective synthesis of 1,2,5,6-tetrahydropyridines (THPs) via proline-catalyzed direct Mannich-cyclization/domino oxidation-reduction sequence: application for medicinally important N-heterocycles

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