Fragment-Based Reaction Discovery of Non-Ene-Type Carbon-Carbon Bond-Forming Reactions: Catalytic Asymmetric Oxetane Synthesis by Screening Olefinic Reactants without Allylic Hydrogen

Koichi Mikami; Kohsuke Aikawa; Junpei Aida

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Fragment-Based Reaction Discovery of Non-Ene-Type Carbon-Carbon Bond-Forming Reactions: Catalytic Asymmetric Oxetane Synthesis by Screening Olefinic Reactants without Allylic Hydrogen

机译：非烯型碳-碳键形成反应的基于片段的反应发现：筛选不带烯丙基氢的烯烃反应物，催化合成不对称环氧乙烷

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Through fragment-based reaction discovery, catalytic asymmetric [2+2] cycloaddition was found to produce oxetanes from trifluoropyruvate and olefinic reactants without allylic hydro-gen. This non-ene-type carbon-carbon bond-forming reaction smoothly proceeded under the influence of chiral Pd or Cu com-plexes as Lewis acid catalysts. The [2+2] cycloaddition afforded the oxetane derivatives in high yields and enantioselectivities even un-der 0.1 mol% catalyst loading and solvent-free conditions.

机译：通过基于片段的反应发现，发现催化不对称[2 + 2]环加成反应可从三氟丙酮酸和烯烃反应物中生成环氧乙烷，而无需烯丙基氢。在作为路易斯酸催化剂的手性Pd或Cu络合物的影响下，这种非烯型碳-碳键形成反应顺利进行。 [2 + 2]环加成反应即使在0.1 mol％的催化剂负载量和无溶剂条件下，也能以高收率和对映选择性提供氧杂环丁烷衍生物。

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《Synlett》 |2011年第18期|共6页
作者
Koichi Mikami; Kohsuke Aikawa; Junpei Aida;
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正文语种 eng
中图分类有机化学理论、物理有机化学;
关键词
fragment-based; Lewis acid catalyst; 2+2 cycloaddi-tion; oxetane; trifluoromethvl;

机译：基于片段的;路易斯酸催化剂;[2 + 2]环氧化;氧杂环丁烷;三氟甲基;

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1. Fragment-Based Reaction Discovery of Non-Ene-Type Carbon-Carbon Bond-Forming Reactions: Catalytic Asymmetric Oxetane Synthesis by Screening Olefinic Reactants without Allylic Hydrogen [J] . Koichi Mikami, Kohsuke Aikawa, Junpei Aida Synlett . 2011,第18期

机译：非烯型碳-碳键形成反应的基于片段的反应发现：筛选不带烯丙基氢的烯烃反应物，催化合成不对称环氧乙烷
2. Stable Axial Chirality in Metal Complexes Bearing 4,4 '-Substituted BIPHEPs: Application to Catalytic Asymmetric Carbon-Carbon Bond-Forming Reactions [J] . Aikawa Kohsuke, Miyazaki Yoshitaka, Mikami Koichi Bulletin of the Chemical Society of Japan . 2012,第2期

机译：金属络合物轴承稳定的轴向手性，轴承4,4' - 取代的Bipheps：应用于催化不对称碳 - 碳键形成反应的应用
3. Catalytic asymmetric carbon-carbon bond-forming reactions in aqueous media [J] . Bhowmick S., Bhowmick K.C. Tetrahedron, Asymmetry: The International Journal for Repid Publication on all Aspects of Asymmetry in Orgainc, Inorganic, Organometallic, Physical and Bio-Organic Chemistry . 2011,第23期

机译：水性介质中催化不对称碳-碳键形成反应
4. C-H Bond Activation by Iridium and Rhodium Complexes: Catalytic Hydrogen-Deuterium Exchange and C-C Bond-Forming Reactions [C] . Steven R. Klei, Klan L. Tan, Jeffrey T. Golden, American Chemical Society National Meeting . 2004

机译：铱和铑配合物的C-H键活化：催化氢 - 氘交换和C-C键形成反应
5. I. Enantioselective total synthesis of quinine and quinidine. II. Thiourea-catalyzed enantioselective C-C bond-forming reactions. a. Catalytic asymmetric N-acyliminium ion cyclizations. b. Catalytic asymmetric aza-Baylis-Hillman reactions [D] . Raheem, Izzat Tiedje 2008

机译：I.奎宁和奎尼丁的对映选择性全合成。二。硫脲催化的对映选择性C-C键形成反应。一个。催化不对称N-酰亚胺离子环化。 b。催化不对称氮杂-Baylis-Hillman反应
6. Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions [O] . Ziya Sahin, Senem Akkoς, İlhan Özer İlhan, 2017

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7. Research on Catalytic Asymmetric Carbon-Carbon Bond-Forming Reactions Utilizing α-Alkylidene β-Oxo Imides [O] . 大山陽文 2015

机译：利用α-亚烷基β-氧代酰亚胺催化不对称碳 - 碳键形成反应的研究

Fragment-Based Reaction Discovery of Non-Ene-Type Carbon-Carbon Bond-Forming Reactions: Catalytic Asymmetric Oxetane Synthesis by Screening Olefinic Reactants without Allylic Hydrogen

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