Enantioselective Assembly of Spirolactones through NHC-Catalyzed Remote γ-Carbon Addition of Enals with Isatins

Rong, Xianfeng; Yao, Hong; Xia, Wei; Du, Yonglei; Zhou, Yu; Liu, Hong

doi:10.1021/acscombsci.5b00197

Cited by 25 publications

(11 citation statements)

References 45 publications

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“…Typical examples involving NHC-catalyzed azolium dienolates by employing the oxidative γ-functionalization of enals are shown in Scheme 63. [91] In 2013, Chi and coworkers reported that the heteroaryl aldehydes containing an indole, benzofuran or benzothiophene moiety also worked well in this process (Scheme 64 with a trifluoromethyl ketone or isatin to form a polycyclic lactone, which contains a quaternary spirocyclic chiral carbon center. The α-branched aryl aldehydes were employed as suitable substrates and gave the corresponding products in moderate to good yields and high enantioselectivities.…”

Section: Scheme 62 Nhc-catalyzed Oxidative [4+2] Cycloaddition Via DImentioning

confidence: 99%

N‐Heterocyclic Carbene Organocatalysis: Activation Modes and Typical Reactive Intermediates

et al. 2020

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N‐Heterocyclic carbene (NHC) organocatalysis has been developed as an important approach in modern organic synthesis. Versatile activation modes within NHC organocatalysis have been established with countless transformations being realized in both efficient and selective fashion. We would like to provide an overview on the key progresses achieved within this field in the past two decades. Since numerous excellent reviews have been documented within this area, we will mainly focus on the scientific development of this research field based on the basic reaction modes and typical reaction intermediates.

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Section: Scheme 62 Nhc-catalyzed Oxidative [4+2] Cycloaddition Via DImentioning

confidence: 99%

N‐Heterocyclic Carbene Organocatalysis: Activation Modes and Typical Reactive Intermediates

et al. 2020

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“…Durch weitere Untersuchungen zur oxidativen Bildung der Spezies VI fanden Liu et al., dass die NHC‐Vorstufe C‐4 ein effizienter Promotor der [4+2]‐Cycloaddition von 13 mit 11 ist (Schema ) . Für die Bildung entsprechender Cycloaddukte 12 , ohne die Verwendung von Lewis‐ oder Brønsted‐Säuren als Cokatalysatoren, wurden gute Ausbeuten und hohe Enantioselektivitäten erzielt.…”

Section: [4+2]‐cycloadditionen Von Carbonylverbindungenunclassified

Katalyse durch N‐heterocyclische Carbene über Azoliumdienolate: eine effiziente Strategie für enantioselektive Funktionalisierungen an entfernten Positionen

et al. 2018

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Die Katalyse durch N‐heterocyclische Carbene (NHCs) ist zu einer effizienten Strategie in der organischen Synthese geworden. In den letzten Jahren wurden etliche Übersichtsartikel veröffentlicht, die NHC‐katalysierte Umwandlungen unter Beteiligung von Breslow‐Intermediaten, Acylazolium‐ und α,β‐ungesättigten Acylazolium‐Intermediaten, Homoenolatäquivalenten sowie Azoliumenolaten behandelten. Doch erst in letzter Zeit wurden durch NHCs erzeugte Azoliumdienolat‐Intermediate in der asymmetrischen Synthese, insbesondere in Cycloadditionen, zur Funktionalisierung entfernter Positionen genutzt. Dieser Kurzaufsatz beleuchtet alle Entwicklungen und neuere Fortschritte für NHC‐katalysierte asymmetrische Cycloadditionen, in denen Azoliumdienolat‐Intermediate auftreten.

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“…2011 年, You 课题组 [38] 2016 年, 我们课题组 [59] 通过以 α,β-不饱和醛 105 为底物, 在 NHC、碳酸铯和氧化剂催化体系中实现了 γ 位的 sp 3 碳活化, 进一步与靛红 104 反应构建出一系列螺内酯类化合物 106 (Scheme 10). 与 Ye 等 [57] 利用酰氯实在之前工作的基础上, Chi 课题组 [60]…”

Section: 羰基化合物 β-碳参与的反应unclassified

Progress of Organic Reactions Catalyzed by N-Heterocyclic Carbenes

Wang¹,

Xiao²,

Zhou³

et al. 2017

Chin. J. Org. Chem.

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Since the first stable N-heterocyclic carbene was isolated by Arduengo in 1991, N-heterocyclic carbine has developed rapidly as a kind of efficient organic catalyst. It plays important role in building complex molecules in organic synthesis for the characteristics of umpolung. Some special Lewis bases and oxidants can induce carbine reaction with carbonyl to form Breslow intermediates, enol and homoenolate, which expand the reaction greatly. In this paper, the recent progresses in organic catalytic reactions including Stetter reaction, a 3-d 3 umpolung catalyzed by carbines are reviewed. Keywords N-heterocyclic carbene; organic catalytic; umpolung 氮杂环卡宾(N-heterocyclic carbene, NHC)的研究历史最早要追溯到 1832 年, Wohler 和 Liebig [1] 发现氰根负离子 (CN-) 可以催化苯甲醛的安息香缩合反应. 随后 Lapworth [2] 对其机理进行研究后发现一分子的苯甲醛在

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Enantioselective Assembly of Spirolactones through NHC-Catalyzed Remote γ-Carbon Addition of Enals with Isatins

Cited by 25 publications

References 45 publications

N‐Heterocyclic Carbene Organocatalysis: Activation Modes and Typical Reactive Intermediates

N‐Heterocyclic Carbene Organocatalysis: Activation Modes and Typical Reactive Intermediates

Katalyse durch N‐heterocyclische Carbene über Azoliumdienolate: eine effiziente Strategie für enantioselektive Funktionalisierungen an entfernten Positionen

Progress of Organic Reactions Catalyzed by N-Heterocyclic Carbenes

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