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

引用次数: 0

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。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

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.