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α-酮酯、2-酰基吡啶和2-酰基吡啶-N-氧化物的催化对映选择性亨利反应。

Catalytic enantioselective Henry reaction of α-keto esters, 2-acylpyridines and 2-acylpyridine -oxides.

作者信息

He Feilong, Chen Guanghui, Yang Junxia, Liang Guojuan, Deng Ping, Xiong Yan, Zhou Hui

机构信息

School of Pharmaceutical Science, Chongqing Medical University Chongqing 400016 PR China

School of Chemistry and Chemical Engineering, Chongqing University Chongqing 401331 PR China.

出版信息

RSC Adv. 2018 Mar 5;8(17):9414-9422. doi: 10.1039/c8ra00552d. eCollection 2018 Feb 28.

Abstract

A pre-prepared Ni-PyBisulidine complex has been developed for the catalytic asymmetric Henry reaction of α-keto esters, 2-acylpyridines and 2-acylpyridine -oxides. The corresponding β-nitro-α-hydroxy esters were obtained in good to excellent yields (up to 99%) with a high enantiomeric excess (ee) (up to 94%) with a catalyst loading of 1-2 mol%. The desired products of 2-acylpyridines and 2-acylpyridine -oxides, which were simple methyl ketones, were obtained in medium to excellent yields (up to 94%) with medium to good ee (up to 86%) by using 2 mol% of catalyst.

摘要

一种预先制备的镍-联吡啶双磺酸配合物已被开发用于α-酮酯、2-酰基吡啶和2-酰基吡啶氧化物的催化不对称亨利反应。在1-2 mol%的催化剂负载量下,相应的β-硝基-α-羟基酯以良好至优异的产率(高达99%)和高对映体过量(ee)(高达94%)获得。对于2-酰基吡啶和2-酰基吡啶氧化物(它们是简单的甲基酮)的所需产物,使用2 mol%的催化剂时,产率为中等至优异(高达94%),对映体过量为中等至良好(高达86%)。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1cd4/9078658/76d4163b0e8d/c8ra00552d-f1.jpg

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