An Organocatalytic Asymmetric Tandem Reaction for the Construction of Bicyclic Skeletons

Chun-Li Cao; You-Yun Zhou; Jian Zhou; Xiu-Li Sun; Yong Tang; Yu-Xue Li; Guang-Yu Li; Jie Sun

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An Organocatalytic Asymmetric Tandem Reaction for the Construction of Bicyclic Skeletons

机译：有机催化不对称串联反应的双环骨架的建设。

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Cyclic ketones react with (E)-2-nitroallylic acetates in the presence of catalytic pyrrolidine-thiourea, which affords bicyclic skeletons with four or five stereocenters in one single reaction with up to 98%ee in moderate to high yields. The cooperative effects of both enamine and the BrOnsted acid are found to be crucial for the high reactivity and enantioselectivity of this cascade reaction, which is demonstrated by both theoretical calculation and experimental data.

机译：环酮在催化吡咯烷-硫脲的存在下与（E）-2-硝基烯丙基乙酸酯反应，在一次反应中可提供具有四个或五个立构中心的双环骨架，产率高达98％ee，中度至高产率。发现烯胺和布朗斯台德酸的协同作用对于该级联反应的高反应性和对映选择性是至关重要的，这在理论计算和实验数据上均得到证明。

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《Chemistry: A European journal》 |2009年第42期|共6页
作者
Chun-Li Cao; You-Yun Zhou; Jian Zhou; Xiu-Li Sun; Yong Tang; Yu-Xue Li; Guang-Yu Li; Jie Sun;
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正文语种 eng
中图分类应用化学;
关键词
bifunctional catalysts; density functional calculations; ketones; organocatalysis; tandem reactions;

机译：双功能催化剂密度泛函计算酮有机催化串联反应;

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1. An Organocatalytic Asymmetric Tandem Reaction for the Construction of Bicyclic Skeletons [J] . Chun-Li Cao, You-Yun Zhou, Jian Zhou, Chemistry: A European journal . 2009,第42期

机译：有机催化不对称串联反应的双环骨架的建设。
2. Enantioselective construction of lactone[2,3-b]piperidine skeletons via organocatalytic tandem reactions [J] . Zhao-Quan He, Bo Han, Rui Li, Organic & biomolecular chemistry . 2010,第4期

机译：通过有机催化串联反应对内酯[2,3-b]哌啶骨架的对映选择性构建
3. Merging Asymmetric Henry Reaction with Organocatalytic Cascade Reaction for the Construction of a Chiral Indolizidine Alkaloid Skeleton [J] . Zhou Yirong, Yang Qin, Shen Jian, The Journal of Organic Chemistry . 2015,第3期

机译：合并不对称亨利反应与有机催化级联反应的手性吲哚并立啶生物碱骨架的建设。
4. An Asymmetric Organocatalytic Domino-Michael-Aldol Reaction [C] . Alexander Kuenkel, Francisco Tato, Magnus Rueping European Symposium on Organic Chemistry . 2009

机译：不对称有机催化多米诺 - Michael-aldol反应
5. Part I. Asymmetric organocatalysis: (1) Direct enantioselective organocatalytic hydroxymethylation of aldehydes catalyzed by alpha,alpha-diphenylprolinol trimethylsilyl ether: Application in the formal synthesis of (-)-Rasfonin; (2) Synthesis of a novel bicyclic secondary amine organocatalyst: Application to the direct enantioselective organocatalytic hydroxymethylation of aldehydes. Part II. Asymmetric synthesis of bicyclic analogues of the anti-osteoporotic drug risedronate. [D] . Miller, John Robert. 2010

机译：第一部分，不对称有机催化：（1）α，α-二苯基脯氨醇三甲基甲硅烷基醚催化的醛的直接对映选择性有机催化羟甲基化：在（-）-Rasfonin的正式合成中的应用；（2）新型双环仲胺有机催化剂的合成：应用于醛的直接对映选择性有机催化羟甲基化。第二部分抗骨质疏松药物Risedronate的双环类似物的不对称合成。
6. Rapid Construction of an Imidazo45-bpyridine Skeleton from 2-Chloro-3-nitropyridinevia Tandem Reaction in H2O-IPA Medium [O] . R. D. Padmaja, †, Vishnu Devi C., 2018

机译：由2-氯-3-硝基吡啶快速构建咪唑并45-b吡啶骨架在H2O-IPA介质中串联反应
7. Bicyclic Carbopalladation Reaction with Twogem-Reaction Centers. Efficient Construction of Fused Bicyclic Skeletons [O] . Shengming Ma, Bin Xu 1999

机译：双环碳弥补反应与扭曲反应中心。高效熔融双环骨骼的建设

An Organocatalytic Asymmetric Tandem Reaction for the Construction of Bicyclic Skeletons

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