Organocatalytic Enantioselective Michael-Michael-Michael-Aldol Condensation Reactions: Control of Six Stereocenters in a Quadruple-Cascade Asymmetric Synthesis of Polysubstituted Spirocyclic Oxindoles

Chaudhari Prakash D.; Hong Bor-Cherng; Lee Gene-Hsiang

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Organocatalytic Enantioselective Michael-Michael-Michael-Aldol Condensation Reactions: Control of Six Stereocenters in a Quadruple-Cascade Asymmetric Synthesis of Polysubstituted Spirocyclic Oxindoles

机译：有机催化对映选择性Michael-Michael-Michael-Aldol缩合反应：控制六个立体封闭在多元级联的不对称合成的六个立体沉积物的多助药梭菌豆类

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An organocatalyzed enantioselective Michael Michael Michael aldol cascade reaction for the construction of cyclopentane fused spirooxindoles was achieved. The domino reaction provided the spirooxindole with six contiguous stereocenters including a quaternary center in good yield's (55-64%) with excellent enantioselectivities (up to >99% ee). Enantioselective Michael Michael Michael aldol condensation-aromatization reactions of an isomeric product were observed.

机译：实现了有机催化的对映选择性Michael Michael Michael aldol级联反应，用于构建环戊烷融合螺氧吲哚氏素。 Domino反应提供螺氧吲哚，具有六个连续的立体封闭，包括季度的季度，产量良好（55-64％），具有优异的对映射性（高达> 99％EE）。观察到异构产物的对映选择性迈克尔迈克尔迈克尔·阿尔德尔·阿尔德氧化芳烃 - 芳烃化反应。

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《Organic letters》 |2017年第22期|共4页
作者
Chaudhari Prakash D.; Hong Bor-Cherng; Lee Gene-Hsiang;
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Natl Chung Cheng Univ Dept Chem &

Biochem Chiayi 621 Taiwan;

Natl Chung Cheng Univ Dept Chem &

Biochem Chiayi 621 Taiwan;

Natl Taiwan Univ Instrumentat Ctr Taipei 106 Taiwan;

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正文语种 eng
中图分类有机化学;
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1. Organocatalytic Enantioselective Michael-Michael-Michael-Aldol Condensation Reactions: Control of Six Stereocenters in a Quadruple-Cascade Asymmetric Synthesis of Polysubstituted Spirocyclic Oxindoles [J] . Chaudhari Prakash D., Hong Bor-Cherng, Lee Gene-Hsiang Organic letters . 2017,第22期

机译：有机催化对映选择性Michael-Michael-Michael-Aldol缩合反应：控制六个立体封闭在多元级联的不对称合成的六个立体沉积物的多助药梭菌豆类
2. Enantioselective synthesis of the tetrahydro-6H-benzo[c]chromenes via Domino Michael-Aldol condensation:control of five stereocenters in a quadruple-cascade organocatalytic multi-component reaction [J] . Prakash Kotame, Bor-Cherng Hong, Ju-Hsiou Liao Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry . 2009,第6期

机译：多米诺迈克尔-奥尔多缩合反应的对映选择性合成四氢-6H-苯并[c]苯二酚：四级联有机催化多组分反应中五个立体中心的控制
3. Enantioselective synthesis of the tetrahydro-6H-benzo[c]chromenes via Domino Michael-Aldol condensation:control of five stereocenters in a quadruple-cascade organocatalytic multi-component reaction [J] . Prakash Kotame, Bor-Cherng Hong, Ju-Hsiou Liao Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry . 2009,第6期

机译：多米诺迈克尔-奥尔多缩合反应的对映选择性合成四氢-6H-苯并[c]苯二酚：四级联有机催化多组分反应中五个立体中心的控制
4. Enantioselective Organocatalytic Cascade Reaction for the Asymmetric Synthesis of Poly substituted Furofuranes [C] . Efraim Reyes, Garazi Talavera, Jose L. Vicario European Symposium on Organic Chemistry . 2009

机译：对聚取代呋喃脲的不对称合成的对映选择性有机催化级联反应
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. Asymmetric Synthesis of Spirocyclopentane OxindolesContaining Four Consecutive Stereocenters and Quaternary α-NitroEsters via Organocatalytic Enantioselective Michael–MichaelCascade Reactions [O] . PrakashD. Chaudhari, Bor-Cherng Hong, *, 2019

机译：螺环戊烷氧化吲哚的不对称合成包含四个连续的立体中心和第四级α-硝基通过有机催化对映选择性迈克尔-迈克尔酯级联反应
7. Organocatalytic Direct Asymmetric Aldol Reactions of 3-Isothiocyanato Oxindoles to Ketones: Stereocontrolled Synthesis of Spirooxindoles Bearing Highly Congested Contiguous Tetrasubstituted Stereocenters [O] . Chen Wen-Bing, Wu Zhi-Jun, Hu Jing, 2011

机译：3-异硫氰酸根合吲哚与酮的有机催化直接不对称醛醇缩合反应：带有高度拥挤的连续四取代的立体中心的螺氧吲哚的立体控制合成。

Organocatalytic Enantioselective Michael-Michael-Michael-Aldol Condensation Reactions: Control of Six Stereocenters in a Quadruple-Cascade Asymmetric Synthesis of Polysubstituted Spirocyclic Oxindoles

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