Ruthenium(II)‐Chitosan, an Enantioselective Catalyst for the Transfer Hydrogenation of N‐Heterocyclic Ketones,ChemCatChem

当前位置： X-MOL 学术 › ChemCatChem › 论文详情

Our official English website, www.x-mol.net, welcomes your feedback! (Note: you will need to create a separate account there.)

Ruthenium(II)‐Chitosan, an Enantioselective Catalyst for the Transfer Hydrogenation of N‐Heterocyclic Ketones
ChemCatChem ( IF 3.8 ) Pub Date : 2019-05-14 , DOI: 10.1002/cctc.201900363
Vanessza Judit Kolcsár ₁ , Ferenc Fülöp _{2,

3} , György Szőllősi ₂

Affiliation

The present study aimed at extending the applicability of a recently developed stereoselective catalytic system to the preparation of optically enriched N‐heterocyclic alcohols. Chiral ruthenium catalyst formed in situ using the chitosan biopolymer as ligand, which provided good results in the transfer hydrogenation of heterobicyclic compounds, such as 4‐chromanone and 4‐thiochromanone, was used in reactions of various N‐containing prochiral ketones. High enantioselectivities were reached in transfer hydrogenations of bicyclic compounds bearing nitrogen either in aromatic or cycloaliphatic moieties, provided that the amino group was protected or shielded by a nearby substituent. Results were rationalized by interactions of the nitrogen with the metal and/or ligand. N‐containing bicyclic compounds having heteroatoms in both rings were also prepared and tested. The detrimental effect of the pyridyl moiety was compensated by the beneficial influence of the heteroatom in the cycloaliphatic ring, as indicated by high rates and good enantioselectivities obtained in reactions of these compounds. Preparation of several N‐heterocyclic alcohols, in good yields and high optical purities was achieved using Ru(II)‐chitosan complex.

中文翻译：

钌（II）-壳聚糖，N-杂环酮转移加氢的对映选择性催化剂

本研究旨在将最近开发的立体选择性催化体系的适用性扩展至光学富集的N-杂环醇的制备。使用壳聚糖生物聚合物作为配体原位形成的手性钌催化剂，在各种N的反应中使用了4-双氢吡喃酮和4-硫代苯并二氢吡喃酮等杂环双环化合物转移加氢的良好结果。含有手性酮。如果氨基被附近的取代基保护或屏蔽，则在芳香族或脂环族部分的含氮双环化合物的转移氢化中，将达到较高的对映选择性。通过氮与金属和/或配体的相互作用合理化结果。Ñ具有还制备和测试在两个环杂原子的含双环化合物。吡啶基部分的有害作用被脂环族环中杂原子的有益影响所补偿，如在这些化合物的反应中获得的高速率和良好的对映选择性所表明的。制备几种氮使用Ru（II）-壳聚糖复合物可实现高收率和高光学纯度的杂环醇。

更新日期：2019-05-14

点击分享查看原文

点击收藏

公开下载

阅读更多本刊新发论文本刊介绍/投稿指南