Ru-catalyzed asymmetric transfer hydrogenation of racemic β-keto γ-lactams via dynamic kinetic resolution

IF 2.1 3区 化学 Q2 CHEMISTRY, ORGANIC Tetrahedron Pub Date : 2024-10-04 DOI:10.1016/j.tet.2024.134293
Pushpa V. Malekar , Ganesh V. More , Chepuri V. Ramana
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Abstract

The enantioselective transfer hydrogenation of racemic β-keto γ-lactams via dynamic kinetic resolution using a chiral Ru(II) catalyst has been developed for the synthesis of optically active β-hydroxyl lactams with excellent conversion (up to 99 %), high diastereomeric ratio (dr 93:07) and enantiomeric selectivity (89 % ee). The reaction proceeded by using HCO2H/Et3N as hydrogen donor and features mild, additive free reaction conditions, fast crystallization, broad substrate scope, and an operationally simpler setup than that for molecular hydrogenation.

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通过动态动力学解析 Ru 催化外消旋 β-酮 γ-内酰胺的不对称转移加氢反应
利用手性 Ru(II) 催化剂,通过动态动力学解析,开发了外消旋β-酮γ-内酰胺的对映选择性转移加氢反应,用于合成光学活性β-羟基内酰胺,该反应具有优异的转化率(高达 99 %)、高非对映异构比(dr 93:07)和对映选择性(89 % ee)。该反应以 HCO2H/Et3N 为氢供体,反应条件温和,不含添加剂,结晶速度快,底物范围广,操作设置比分子氢化简单。
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来源期刊
Tetrahedron
Tetrahedron 化学-有机化学
CiteScore
3.90
自引率
4.80%
发文量
439
审稿时长
34 days
期刊介绍: Tetrahedron publishes full accounts of research having outstanding significance in the broad field of organic chemistry and its related disciplines, such as organic materials and bio-organic chemistry. Regular papers in Tetrahedron are expected to represent detailed accounts of an original study having substantially greater scope and details than that found in a communication, as published in Tetrahedron Letters. Tetrahedron also publishes thematic collections of papers as special issues and ''Reports'', commissioned in-depth reviews providing a comprehensive overview of a research area.
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