N-heterocyclic carbene-catalyzed homoenolate additions with N-Aryl ketimines as electrophiles: Efficient synthesis of spirocyclic γ-lactam oxindoles

Zhang B.; Feng P.; Sun L.-H.; Cui Y.; Ye S.; Jiao N.

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N-heterocyclic carbene-catalyzed homoenolate additions with N-Aryl ketimines as electrophiles: Efficient synthesis of spirocyclic γ-lactam oxindoles

机译：以N-芳基酮亚胺为亲电体的N-杂环卡宾催化的均烯酸酯加成反应：螺环γ-内酰胺ox吲哚的高效合成

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摘要

In pole position: A simple and efficient approach to spirocyclic γ-lactam oxindoles by the N-heterocyclic carbene catalyzed addition of homoenloate equivalents to N-aryl isatinimines has been developed (see scheme). The use of N-aryl isatinimines as electrophiles in the NHC-catalyzed umpolung reaction of α,β-unsaturated aldehydes is demonstrated for the first time.

机译：处于极点：已开发出一种简单有效的方法，通过N杂环卡宾催化的均烯酸酯等效物加成到N-芳基异亚胺基上来合成螺环γ-内酰胺羟吲哚（参见方案）。首次证明了在NHC催化的α，β-不饱和醛的umpolung反应中使用N-芳基异亚胺作为亲电子试剂。

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《Chemistry: A European journal》 |2012年第30期|共6页
作者
Zhang B.; Feng P.; Sun L.-H.; Cui Y.; Ye S.; Jiao N.;
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正文语种 eng
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关键词
carbenes; lactams; organocatalysis; spiro compounds; umpolung;

机译：卡宾;内酰胺;有机催化;螺类化合物;药物;

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1. N-heterocyclic carbene-catalyzed homoenolate additions with N-Aryl ketimines as electrophiles: Efficient synthesis of spirocyclic γ-lactam oxindoles [J] . Zhang B., Feng P., Sun L.-H., Chemistry: A European journal . 2012,第30期

机译：以N-芳基酮亚胺为亲电体的N-杂环卡宾催化的均烯酸酯加成反应：螺环γ-内酰胺ox吲哚的高效合成
2. Asymmetric Synthesis of Spirocyclic Oxindole delta-Lactams via NHC-Catalyzed Formal [2+4] Annulation of Aliphatic Aldehydes with Oxindole-Derived alpha,beta-Unsaturated Ketimines [J] . He Chonglong, Li Zhanhuan, Xu Jianfeng, The Journal of Organic Chemistry . 2019,第18期

机译：通过NHC催化的脂醛α，脂肪醛α，β-不饱和酮肟的NHC催化正式[2 + 4]环的不对称合成螺旋环氧丁胺δ-内酰胺。
3. Enantioselective N-Heterocyclic Carbene-Catalyzed Synthesis of Spirocyclic Oxindole-benzofuroazepinones [J] . Gao Zhong-Hua, Chen Kun-Quan, Zhang Yan, The Journal of Organic Chemistry . 2018,第24期

机译：对苯并环苯甲酰苯并呋喃酮的对映选择性的N-杂环碳酸催化合成
4. N-Heterocyclic Carbene-Catalyzed Synthesis of α-Amino Ketonesfrom in Situ-Produced Imines Derived from Aminals [C] . Justin Lamb, Ryo Takashima, Yumiko Suzuki 日本化学会春季年会 . 2020

机译：衍生自芳基的原位产生的亚胺中的N-杂环促α-氨基酮的合成
5. Progress toward the first total synthesis of (-)-gelsemicine and new spirocyclic oxindole synthesis based on a hetero Claisen rearrangement. [D] . Mao, Zhan. 2005

机译：迈向第一个完全合成（-）-gelsemicine和基于杂化Claisen重排的新螺环羟吲哚合成的进展。
6. Cyclic Ketimines as Superior Electrophiles for NHC-Catalyzed Homoenolate Additions with Broad Scope and Low Catalyst Loadings [O] . Michael Rommel, Takeo Fukuzumi, Jeffrey W. Bode -1

机译：环状酮亚胺类化合物作为NHC催化的均方酸加成物的优良亲电试剂具有广泛的作用范围和低的催化剂负载量
7. N-Heterocyclic Carbene-Catalyzed Reaction of Chalcones and Enals via Homoenolate: an Efficient Synthesis of 1, 3, 4-Trisubstituted Cyclopentenes [O] . -1

机译：通过均酚酸盐酸盐和烯酮的N-杂环催化Chalcone和Enals的反应：高效合成1,3,4-三取代的环戊烯酮

N-heterocyclic carbene-catalyzed homoenolate additions with N-Aryl ketimines as electrophiles: Efficient synthesis of spirocyclic γ-lactam oxindoles

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