Resin-immobilized pyrrolidine-based chiral organocatalysts for asymmetric Michael additions of ketones and aldehydes to nitroolefins

Zhang Richeng; Yin Guohui; Li Yang; Yan Xilong; Chen Ligong

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Resin-immobilized pyrrolidine-based chiral organocatalysts for asymmetric Michael additions of ketones and aldehydes to nitroolefins

机译：基于树脂固定化的基于吡咯烷的手性有机催化剂，用于非对称Michael添加酮和醛至亚硝酸酯

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Based on the electrostatic adsorption between acidic resins and organocatalysts, a series of resin-supported chiral organocatalysts were designed and synthesized. They were evaluated for the asymmetric Michael addition of cyclohexanone with nitrostyrene, in which, catalyst 3 (Fig. 1) exhibited the best catalytic performance. This reaction proceeded under catalyst 3 smoothly at room temperature without any solvent or additive and could give product with high yield (95%) and good stereoselectivity (90% ee, 98 : 2 dr). Encouragingly, catalyst 3 was easily isolated and reused for 16 consecutive runs without obvious loss of reaction enantioselectivity. Furthermore, it was successfully applied to catalyze the reactions of a series of ketones and aldehydes with nitroolefins.

机译：基于酸性树脂和有机催化剂之间的静电吸附，设计并合成了一系列树脂负载的手性有机催化剂。评估它们用硝基丁烯的环己酮加入不对称的迈克啉，其中催化剂3（图1）表现出最佳的催化性能。该反应在室温下平滑地在催化剂3下进行，没有任何溶剂或添加剂，并且可以给予高产率（95％）和良好的立体选择性（90％EE，98：2 DR）的产物。令人鼓舞的是，催化剂3容易被隔离并重复使用16个连续运行，而不会明显丧失反应映射性。此外，成功地应用于催化一系列酮和醛与亚硝烯烃的反应。

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《RSC Advances》 |2015年第5期|共4页
作者
Zhang Richeng; Yin Guohui; Li Yang; Yan Xilong; Chen Ligong;
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作者单位

Tianjin Univ Sch Chem Engn &

Technol Tianjin 300072 Peoples R China;

Tianjin Univ Sch Chem Engn &

Technol Tianjin 300072 Peoples R China;

Tianjin Univ Sch Chem Engn &

Technol Tianjin 300072 Peoples R China;

Tianjin Univ Sch Chem Engn &

Technol Tianjin 300072 Peoples R China;

Tianjin Univ Sch Chem Engn &

Technol Tianjin 300072 Peoples R China;

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正文语种 eng
中图分类化学;
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1. Resin-immobilized pyrrolidine-based chiral organocatalysts for asymmetric Michael additions of ketones and aldehydes to nitroolefins [J] . Zhang Richeng, Yin Guohui, Li Yang, RSC Advances . 2015,第5期

机译：基于树脂固定化的基于吡咯烷的手性有机催化剂，用于非对称Michael添加酮和醛至亚硝酸酯
2. Direct Asymmetric Michael Additions of Ketones to Nitroolefins and Chalcones Catalyzed by a Chiral C2-Symmetric Pyrrolidine-based Tetraamine [J] . 马世俊, 吴璐璐, 刘明, 中国化学（英文版） . 2012,第011期

机译：手性C2对称的吡咯烷基四胺催化的酮类化合物向硝基烯烃和查尔酮的直接不对称迈克尔加成反应
3. The Use of N-Alkyl-2,2'-bipyrrolidine Derivatives as Organocatalysts for the Asymmetric Michael Addition of Ketones and Aldehydes to Nitroolefins [J] . Olivier Andrey, Alexandre Alexakis, Alex Tomassini Advanced synthesis & catalysis . 2004,第9a10期

机译：N-烷基-2,2'-联吡咯烷衍生物作为有机催化剂用于酮和醛不对称加成至硝基烯烃的有机催化剂
4. Asymmetric Michael Addition Reaction of α-Aminomaleimides to β-Nitroolefins Using an Organocatalyst [C] . Naoki Sakai, Masashi Kajitani, Takeshi Oriyama 日本化学会春季年会 . 2020

机译：使用有机催化剂的α-氨基酰胺酰胺对β-亚烯烃的不对称迈克尔添加反应
5. Part I. Asymmetric synthesis of bicyclic analogues of risedronate as molecular probes of the mechanism of action of bisphosphonate antiosteoporotic drugs and potentially more efficacious antiosteoporotic agents. Part II. Facile preparation and functionalization of chiral stabilized ylides from common chiral auxiliaries using the Bestmann ylide and their use in Wittig reactions. Part III. Asymmetric organocatalysis: 1. An investigation of alpha-hydroxylation of aldehydes; 2. Synthesis of a novel camphor-based alpha-aminotetrazole organocatalyst. [D] . Song, Xinyi. 2007

机译：第一部分：利塞膦酸盐双环类似物的不对称合成，作为双膦酸盐类抗骨质疏松药和潜在更有效的抗骨质疏松药作用机理的分子探针。第二部分使用Bestmann内酯从常见手性助剂轻松制备和官能化手性稳定化的叶基及其在Wittig反应中的用途。第三部分不对称有机催化：1.醛的α-羟基化研究； 2.合成新的基于樟脑的α-氨基四唑有机催化剂。
6. Synthesis of new pyrrolidine-based organocatalysts and study of their use in the asymmetric Michael addition of aldehydes to nitroolefins [O] . Alejandro Castán, Ramón Badorrey, José A Gálvez, 2017

机译：新型吡咯烷基有机催化剂的合成及其在醛不对称加成至硝基烯烃中的研究
7. Synthesis of new pyrrolidine-based organocatalysts and study of their use in the asymmetric Michael addition of aldehydes to nitroolefins [O] . Alejandro Castán, Ramón Badorrey, José A. Gálvez, 2017

机译：新型吡咯烷类有机催化剂的合成及其在醛与硝基烯烃不对称迈克尔加成中的应用研究
8. Addition Compounds of Alkali Metal Hydrides. 32. A Comparison Study of Chiral Trialkylborohydrides and Chiral Dialkylmonoalkoxyborohydrides for the Asymmetric Reduction of Prochiral Ketones: The Effect of Comparable Chiral Alkyl a [R] . Brown, H. C., Park, W. S., Cho, B. T. 1987

机译：碱金属氢化物的加成化合物。 32.手性三烷基硼氢化物和手性二烷基单烷氧基硼氢化物对前手性酮不对称还原的比较研究：可比较的手性烷基a的影响

Resin-immobilized pyrrolidine-based chiral organocatalysts for asymmetric Michael additions of ketones and aldehydes to nitroolefins

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