Enantioselective synthesis of tunable chiral pyridine–aminophosphine ligands and their applications in asymmetric hydrogenation,Organic & Biomolecular Chemistry

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Enantioselective synthesis of tunable chiral pyridine–aminophosphine ligands and their applications in asymmetric hydrogenation
Organic & Biomolecular Chemistry ( IF 2.9 ) Pub Date : 2019-05-01 , DOI: 10.1039/c9ob00770a
Youran Liu _{1,

2,

3,

4,

5} , Fei Chen _{1,

2,

3,

4,

5} , Yan-Mei He _{1,

2,

3,

4,

5} , Chenghao Li _{1,

2,

3,

4,

5} , Qing-Hua Fan _{1,

2,

3,

4,

5}

Affiliation

A small library of tunable chiral pyridine–aminophosphine ligands were enantioselectively synthesized based on chiral 2-(pyridin-2-yl)-substituted 1,2,3,4-tetrahydroquinoline scaffolds, which were obtained in high yields and with excellent enantioselectivities via ruthenium-catalyzed asymmetric hydrogenation of 2-(pyridin-2-yl)quinolines. The protocol features a wide substrate scope and mild reaction conditions, enabling scalable synthesis. These chiral P,N ligands were successfully applied in the Ir-catalyzed asymmetric hydrogenation of benchmark olefins and challenging seven-membered cyclic imines including benzazepines and benzodiazepines. Excellent enantio- and diastereoselectivity (up to 99% ee and >20 : 1 dr), and/or unprecedented chemoselectivity were obtained in the asymmetric hydrogenation of 2,4-diaryl-3H-benzo[b]azepines and 2,4-diaryl-3H-benzo[b][1,4]diazepines.

中文翻译：

可调谐手性吡啶-氨基膦配体的对映选择性合成及其在不对称氢化中的应用

基于手性2-（吡啶-2-基）-取代的1,2,3,4-四氢喹啉骨架，对映选择性地合成了一个可调谐的手性吡啶-氨基膦配体的小型文库，该文库以高收率和优异的对映选择性通过钌催化的2-（吡啶-2-基）喹啉不对称氢化。该方案具有广泛的底物范围和温和的反应条件，可实现可扩展的合成。这些手性P，N配体已成功应用于Ir催化的基准烯烃和具有挑战性的七元环亚胺（包括苯并ze庚因和苯并二氮杂卓）的不对称加氢反应。在2,4-二芳基-3 H-苯并[ b ]氮杂和2,4-不对称氢化反应中，具有出色的对映和非对映选择性（高达99％ee和> 20：1 dr）和/或前所未有的化学选择性。二芳基-3 H-苯并[ b ] [1,4]二氮杂pine。

更新日期：2019-05-22

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