Catalytic enantioselective Henry reaction of alpha-keto esters, 2-acylpyridines and 2-acylpyridine N-oxides

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

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Catalytic enantioselective Henry reaction of alpha-keto esters, 2-acylpyridines and 2-acylpyridine N-oxides

机译：α-酮酯，2-酰基吡啶和2-酰基吡啶N-氧化物催化对映选择性亨利反应

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A pre-prepared Ni-PyBisulidine complex has been developed for the catalytic asymmetric Henry reaction of alpha-keto esters, 2-acylpyridines and 2-acylpyridine N-oxides. The corresponding beta-n 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 N-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.

机译：已经为α-酮酯，2-酰基吡啶和2-酰吡啶N-氧化物的催化不对称亨利反应开发了预先制备的Ni-Pybiusulidine络合物。相应的β-羟基酯是良好的优异产率（高达99％），具有高对映体过量（EE）（高达94％），催化剂负载为1-2摩尔％。通过使用2mol％，在培养基中获得2-酰基吡啶和2-酰基吡啶N-氧化物的所需产物，其单纯于甲基酮，以优异的产率（高达94％）（高达86％）获得催化剂。

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来源
《RSC Advances》 |2018年第17期|共9页
作者
He Feilong; Chen Guanghui; Yang Junxia; Liang Guojuan; Deng Ping; Xiong Yan; Zhou Hui;
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Chongqing Med Univ Sch Pharmaceut Sci Chongqing 400016 Peoples R China;

Chongqing Med Univ Sch Pharmaceut Sci Chongqing 400016 Peoples R China;

Chongqing Med Univ Sch Pharmaceut Sci Chongqing 400016 Peoples R China;

Chongqing Med Univ Sch Pharmaceut Sci Chongqing 400016 Peoples R China;

Chongqing Med Univ Sch Pharmaceut Sci Chongqing 400016 Peoples R China;

Chongqing Univ Sch Chem &

Chem Engn Chongqing 401331 Peoples R China;

Chongqing Med Univ Sch Pharmaceut Sci Chongqing 400016 Peoples R China;

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正文语种 eng
中图分类化学;
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1. Catalytic enantioselective Henry reaction of alpha-keto esters, 2-acylpyridines and 2-acylpyridine N-oxides [J] . He Feilong, Chen Guanghui, Yang Junxia, RSC Advances . 2018,第17期

机译：α-酮酯，2-酰基吡啶和2-酰基吡啶N-氧化物催化对映选择性亨利反应
2. Enantioselective Addition of Nitromethane to 2-Acylpyridine N-Oxides. Expanding the Generation of Quaternary Stereocenters with the Henry Reaction [J] . Melireth Holmquist, Gonzalo Blay, M. Carmen Mu?oz, Organic letters . 2014,第4期

机译：硝基甲烷向2-酰基吡啶N-氧化物的对映选择性加成。利用亨利反应扩大四元立体中心的生成
3. Multiselective Catalytic Asymmetric Reactions Using alpha-Keto Esters as Pronucleophiles [J] . Sohtome Yoshihiro, Sodeoka Mikiko Synlett . 2020,第6期

机译：使用α-酮酯作为前后核心的多元催化不对称反应
4. Enantioselective Direct Mannich-Type Reactions of 2-Benzylpyridine N-Oxides Catalyzed by Chiral Bis(guanidino)iminophosphorane Organosuperbase [C] . Qiupeng Hu, Azusa Kondoh, Masahiro Terada 日本化学会春季年会講演予稿集 . 2018

机译：由手性双（胍基）催化的2-苄基吡啶N-氧化物的对映选择性直接曼尼希型反应
5. Catalytic enantioselective synthesis of O-and N-substituted quaternary carbon stereogenic centers: 1. Aluminum-catalyzed alkylations of alpha-ketoesters with dialkylzinc reagents. 2. Silver-catalyzed vinylogous Mannich-type reactions of alpha-ketoimine esters with siloxyfurans [D] . Wieland, Laura Caroline 2008

机译：O和N取代的季碳立构中心的催化对映选择性合成：1.用二烷基锌试剂进行铝催化的α-酮酸酯的烷基化。 2.α-酮亚胺酯与甲硅烷氧基呋喃的银催化乙烯基曼尼希型反应
6. Asymmetric Henry Reaction of 2-Acylpyridine N-Oxides Catalyzed by a Ni-Aminophenol Sulfonamide Complex: An Unexpected Mononuclear Catalyst [O] . Mouxiong Liu, Dongdong Gui, Ping Deng, 2019

机译：Ni-氨基苯酚磺酰胺配合物催化的2-酰基吡啶N-氧化物的不对称亨利反应：一种意外的单核催化剂
7. Catalytic enantioselective Henry reaction of α-keto esters, 2-acylpyridines and 2-acylpyridine N-oxides [O] . Feilong He, Guanghui Chen, Junxia Yang, 2018

机译：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 alpha-keto esters, 2-acylpyridines and 2-acylpyridine N-oxides

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