Enantioselective Formal C(sp(2))-H Vinylation

Manna Madhu Sudan; Sarkar Rahul; Mukherjee Santanu

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Enantioselective Formal C(sp(2))-H Vinylation

机译：对映选择性形式C（sp（2））-H乙烯基化

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An enantioselective formal C(sp(2))-H vinylation of prochiral 2,2-disubstituted cyclopentene-1,3-dione is presented. This vinylative desymmetrization is realized by using a two-step procedure that consists of a catalytic enantioselective vinylogous Michael addition of deconjugated butenolides to cyclopentene-1,3-dione and a base-mediated decar-boxylation. The overall process utilizes deconjugated butenolides as the source of the highly substituted vinyl unit. Five-membered carbocycles containing a remote all-carbon quaternary stereogenic center are obtained in good yields and with good to high enantioselectivities.

机译：提出了对映体形式C（sp（2））-H手性2,2-二取代环戊烯-1,3-二酮的乙烯基化。该乙烯基化脱对称化是通过使用两步程序实现的，该程序包括将解偶联的丁烯内酯向环戊烯-1,3-二酮进行催化的对映体选择性乙烯基迈克尔加成反应，以及由碱介导的十烷基化反应。整个过程利用去共轭的丁烯内酯作为高度取代的乙烯基单元的来源。以高收率和良好至高对映选择性获得了含有偏远全碳四元立体构象中心的五元碳环。

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《Chemistry: A European journal》 |2016年第42期|共8页
作者
Manna Madhu Sudan; Sarkar Rahul; Mukherjee Santanu;
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正文语种 eng
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C-H functionalization; decarboxylation; desymmetrization; lactones; vinylation;

机译：碳氢官能化脱羧脱对称内酯乙烯基化;

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1. Enantioselective Formal C(sp(2))-H Vinylation [J] . Manna Madhu Sudan, Sarkar Rahul, Mukherjee Santanu Chemistry: A European journal . 2016,第42期

机译：对映选择性形式C（sp（2））-H乙烯基化
2. Palladium-catalyzed diastereo- and enantioselective formal [3+2] cycloaddition of vinyl cyclopropanes with cyclic 1-azadienes [J] . Zhou Qing, Chen Bo, Huang Xiao-Bing, Organic Chemistry Frontiers . 2019,第11期

机译：钯 - 催化的非对映号和对致注色的正式[3 + 2]环加成乙烯基环丙烷与环状1-己烯酮
3. An unusual stereoretentive 1,3-quaternary carbon shift resulting in an enantioselective RhII-catalyzed formal [4+1]-cycloaddition between diazo compounds and vinyl ketenes [J] . Kevin X. Rodriguez, Tara C. Pilato, Brandon L. Ashfeld Chemical science . 2018,第12期

机译：一种不寻常的立体保留1，3-季碳转移，导致重氮化合物与乙烯基烯酮之间的对映选择性RhII催化的正式[4 + 1]-环加成
4. Chiral Bronsted Acid-Catalyzed Formal α-Vinylation of Ketones for the Enantioselective Construction of Quaternary Carbon Centre [C] . Satavisha Kayal, Jun Kikuchi, Masahiro Terada 日本化学会春季年会講演予稿集 . 2018

机译：酮的手性抗正囊催化正式α-乙烯基化用于季碳中心的映选择性建设
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. An unusual stereoretentive 13-quaternary carbon shift resulting in an enantioselective RhII-catalyzed formal 4+1-cycloaddition between diazo compounds and vinyl ketenes [O] . Kevin X. Rodriguez, Tara C. Pilato, Brandon L. Ashfeld 2018

机译：一种不寻常的立体保留13-季碳转移导致重氮化合物与乙烯基烯酮之间的对映选择性RhII催化的正式4 + 1-环加成
7. Palladium-Catalyzed Diastereo- and Enantioselective Synthesis of Substituted Cyclopentanes through a Dynamic Kinetic Asymmetric Formal 3+2-Cycloaddition of Vinyl Cyclopropanes and Alkylidene Azlactones [O] . Barry M. Trost, Patrick J. Morris 2011

机译：通过动态动态动力学非对称形式的乙烯基环丙烷和亚烷基甲烷酮的钯催化取代环戊烷的钯 - 催化和对取代的环戊烷的对致映选择性合成

Enantioselective Formal C(sp(2))-H Vinylation

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