Organocatalytic Enantioselective Michael/Cyclization Domino Reaction between 3-Amideoxindoles and alpha,beta-Unsaturated Aldehydes: One-Pot Preparation of Chiral Spirocyclic Oxindole-gamma-Iactams

Yang Peng; Wang Xiao; Chen Feng; Zhang Zheng-Bing; Chen Chao; Peng Lin; Wang Li-Xin

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Organocatalytic Enantioselective Michael/Cyclization Domino Reaction between 3-Amideoxindoles and alpha,beta-Unsaturated Aldehydes: One-Pot Preparation of Chiral Spirocyclic Oxindole-gamma-Iactams

机译：有机催化映选择性迈克尔/环化多米诺3- amideoxindoles和α，β-不饱和醛：一锅制剂手性螺环氧吲哚-γ-γ-γ蛋白

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The first organocatalytic enantioselective Michael/ cydization domino reaction between 3-amideoxindoles and alpha,beta-unsaturated aldehydes is described. After sequential oxidation with pyridinium chlorochromate, a direct and one-pot preparation of highly sterically hindered spirocyclic oxindole-gamma-lactams was achieved in 51-81% yields with 75-97% ee and <= 80/20 dr.

机译：描述了第一种有机催化对映选择性迈克尔/三种吲哚吲哚和α，β-不饱和醛之间的酶联反应。用吡啶鎓氯化物氢氧化氢氧化后，在51-81％的产率和<= 80/20博物中，在51-81％的产率下实现了高度间受阻螺梭氧胆碱 - γ-γ-γ-γ-γ-γ-γ-γ-γ-γ-γ-γ-γ-γ-γ-丙胺。

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《The Journal of Organic Chemistry》 |2017年第7期|共9页
作者
Yang Peng; Wang Xiao; Chen Feng; Zhang Zheng-Bing; Chen Chao; Peng Lin; Wang Li-Xin;
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作者单位

Chinese Acad Sci Chengdu Inst Organ Chem Key Lab Asymmetr Synth &

Chirotechnol Sichuan Pro Chengdu 610041 Peoples R China;

Chinese Acad Sci Chengdu Inst Organ Chem Key Lab Asymmetr Synth &

Chirotechnol Sichuan Pro Chengdu 610041 Peoples R China;

Chinese Acad Sci Chengdu Inst Organ Chem Key Lab Asymmetr Synth &

Chirotechnol Sichuan Pro Chengdu 610041 Peoples R China;

Chinese Acad Sci Chengdu Inst Organ Chem Key Lab Asymmetr Synth &

Chirotechnol Sichuan Pro Chengdu 610041 Peoples R China;

Chinese Acad Sci Chengdu Inst Organ Chem Key Lab Asymmetr Synth &

Chirotechnol Sichuan Pro Chengdu 610041 Peoples R China;

Chinese Acad Sci Chengdu Inst Organ Chem Key Lab Asymmetr Synth &

Chirotechnol Sichuan Pro Chengdu 610041 Peoples R China;

Chinese Acad Sci Chengdu Inst Organ Chem Key Lab Asymmetr Synth &

Chirotechnol Sichuan Pro Chengdu 610041 Peoples R China;

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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/Cyclization Domino Reaction between 3-Amideoxindoles and alpha,beta-Unsaturated Aldehydes: One-Pot Preparation of Chiral Spirocyclic Oxindole-gamma-Iactams [J] . Yang Peng, Wang Xiao, Chen Feng, The Journal of Organic Chemistry . 2017,第7期

机译：有机催化映选择性迈克尔/环化多米诺3- amideoxindoles和α，β-不饱和醛：一锅制剂手性螺环氧吲哚-γ-γ-γ蛋白
2. Enantioselective synthesis of syn-2-amino-1,3-diols via organocatalytic sequential oxa-Michael/alpha-amination reactions of alpha,beta-unsaturated aldehydes [J] . Weng Jiang, Huang Lin-Jie, Long Liang, Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry . 2016,第23期

机译：通过有机催化顺序的α，β-不饱和醛的oxa-Michael /α-氨基化反应对对-2-氨基-1,3-二醇的对映选择性合成
3. Organocatalytic enantioselective domino Michael-aldol condensation of 5-oxoalkanal and alpha,beta-unsaturated aldehydes. Efficient assembly of densely functionalized cyclohexenes [J] . Hong BC, Nimje RY, Sadani AA, Organic letters . 2008,第12期

机译：5-氧代烷醛与α，β-不饱和醛的有机催化对映选择性多米诺骨牌迈克尔-奥尔多缩合反应。高效组装密集功能化的环己烯
4. Enantioselective 2+2 Cycloaddition Reaction of 1-Methoxyallenylsilane with alpha-Imino Ester:Chiral Synthesis of alpha,beta-Unsaturated Acylsilanes [C] . Kazunori Daidouji, Kohei Fuchibe, Takahiko Akiyama Symposium on Organometallic Chemistry . 2003

机译：1-甲氧基亚乙烷与α-亚氨基酯的映选择性2 + 2环加入反应：α，β-不饱和酰基硅烷的手性合成
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. Organocatalytic cascade aza-Michael/hemiacetal reaction between disubstituted hydrazines and αβ-unsaturated aldehydes: Highly diastereo- and enantioselective synthesis of pyrazolidine derivatives [O] . Zhi-Cong Geng, Jian Chen, Ning Li, 2012

机译：双取代肼与αβ-不饱和醛之间的有机催化级联氮杂-迈克尔/半缩醛反应：吡唑烷衍生物的高度非对映和对映选择性合成
7. Enantioselective Organocatalytic Tandem Michael-Aldol Reactions: One-Pot Synthesis of Chiral Thiochromenes [O] . -1

机译：对映选择性有机催化串联迈克尔 - 醛醇反应：单罐合成手性硫代噻吩

Organocatalytic Enantioselective Michael/Cyclization Domino Reaction between 3-Amideoxindoles and alpha,beta-Unsaturated Aldehydes: One-Pot Preparation of Chiral Spirocyclic Oxindole-gamma-Iactams

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