Squaramide-catalysed asymmetric cascade reactions of 2,3-dioxopyrrolidines with 3-chlorooxindoles

Wen, Jiang-Bo; Du, Dan

doi:10.1039/c9ob02663k

Cited by 18 publications

(7 citation statements)

References 31 publications

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“…Later in 2020, Du reported a related reaction using this time 3‐chlorooxindoles as pronucleophiles. Again, the reaction was catalyzed by a bifunctional squaramide derivative of quinine C14 [80] . The authors found that the presence of one equivalent of NH 4 HCO 3 was crucial to obtain the desired bi‐spirocyclic products in high yields, diastereoselectivities and enantiomeric excesses (Scheme 51).…”

Section: ‐Ylidene‐23‐dioxopyrrolidinesmentioning

confidence: 99%

Asymmetric Addition and Cycloaddition Reactions with Ylidene‐Five‐Membered Heterocycles

et al. 2021

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Five‐membered heterocycles bearing an exocyclic double bond have been successfully used as substrates in asymmetric addition and cycloaddition reactions. Ylidene‐heterocycles are attractive substrates due to their high functionalization and the presence of an electrophilic conjugated exocyclic double bound that can participate in nucleophilic addition reactions as well as cycloaddition reactions, which may be triggered by the formation of aromatic intermediates or products in many cases. During the last decades, catalytic methodologies have been developed using ylidene‐heterocycles as substrates in order to synthesize useful optically active heterocyclic derivatives. 4‐Ylidene‐pyrazol‐5‐ones, isoxazolin‐5‐ones, 2,3‐dioxopyrrolidines, rhodanines, oxazolidindiones, Erlenmeyer‐Ploch azlactones and 5‐ylidene‐thiazolones have been successfully used as substrates in asymmetric reactions. This review collects the powerful research in asymmetric addition and cycloaddition reactions where ylidene‐five‐membered heterocycles have been used.

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Section: ‐Ylidene‐23‐dioxopyrrolidinesmentioning

confidence: 99%

Asymmetric Addition and Cycloaddition Reactions with Ylidene‐Five‐Membered Heterocycles

et al. 2021

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“…Chiral squaramide has been shown to successfully catalyze several reactions including Michael additions, and the Mannich, aza-Henry, and Strecker reactions. Moreover, these catalysts have successfully produced enantio-enriched products in single and domino/cascade reactions in various asymmetric organic transformations [168][169][170][171][172][173][174][175][176].…”

Section: Squaramide Catalystmentioning

confidence: 99%

Regiodivergent Organocatalytic Reactions

et al. 2021

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Organocatalysts are abundantly used for various transformations, particularly to obtain highly enantio- and diastereomeric pure products by controlling the stereochemistry. These applications of organocatalysts have been the topic of several reviews. Organocatalysts have emerged as one of the very essential areas of research due to their mild reaction conditions, cost-effective nature, non-toxicity, and environmentally benign approach that obviates the need for transition metal catalysts and other toxic reagents. Various types of organocatalysts including amine catalysts, Brønsted acids, and Lewis bases such as N-heterocyclic carbene (NHC) catalysts, cinchona alkaloids, 4-dimethylaminopyridine (DMAP), and hydrogen bond-donating catalysts, have gained renewed interest because of their regioselectivity. In this review, we present recent advances in regiodivergent reactions that are governed by organocatalysts. Additionally, we briefly discuss the reaction pathways of achieving regiodivergent products by changes in conditions such as solvents, additives, or the temperature.

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“…图式 5 3-氨基氧吲哚与乙烯基磺酰氟的 Michael/环化串联反应 Scheme 5 Michael/cyclization cascade reactions of 3-aminooxindoles with ethylene sulfonyl fluorides 他骨架底物, 分别于 2019 年 [21] 和 2020 年 [22] (1) R 1 = CO 2 Et, CO 2 Me, Boc; R 2 = Boc, Me, Bn, Ac; R 3 = 5-OMe, 5-Cl, 6-Cl, 7-Cl, 5-NO 2 ; R 4 = Ph, 4-ClC 6 H 4 , 4-MeOC 6 H 4 , Me; R 5 = 6-Cl, 6-OMe, 7-OMe, 5-OH 随后, 2018 年, 本课题组 [28] 9.2 3-三氟乙基亚胺氧吲哚参与的不对称 1,3-偶极环化串联反应同年, 王锐等 [39] 利用本课题组所开发的新型氧吲哚串联反应试剂 3-三氟乙基亚胺氧吲哚 2g [40] 2017 年, 鲁桂课题组 [43] 利用 3-亚甲基氧吲哚 2b 与 3-三氟乙基亚胺氧吲哚 2g 反应, 报道了一例选择性环外 1,3-偶极环化串联反应(Scheme 19a). 在奎宁衍生的方酰胺 C14 催化作用下, 以高度立体选择性的方式有效地构建了一系列潜在的具有重要生物学意义的含三氟甲基的吡咯烷基螺环双氧吲哚产物 80 (84%～99%的产率, 高达＞20∶1 dr 和＞99% ee).…”

Section: 方酰胺催化的不对称 Michael/环化串联反应unclassified

Recent Advances in Squaramide-Catalyzed Asymmetric Cascade Reactions for the Synthesis of Spirooxindoles

Lin¹,

Du²

2020

Chin. J. Org. Chem.

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Chiral spirooxindoles have captured huge attention from researchers in the area of organic chemistry and medicinal chemistry owing to their prevalence in various alkaloid natural products and pharmacologically active agents. In recent year, chiral bifunctional squaramide-catalyzed asymmetric cascade reaction of oxindoles or oxindole derivatives has become an efficient synthetic method for the construction of chiral spirooxindoes. In this review, the remarkable progress and advances in bifunctional squaramide-catalyzed asymmetric cascade reactions for the synthesis of spirooxindole derivatives from 2015 are summarized and discussed based on the different types of catalytic reactions.

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Squaramide-catalysed asymmetric cascade reactions of 2,3-dioxopyrrolidines with 3-chlorooxindoles

Abstract: An efficient squaramide-catalysed asymmetric Michael addition/cyclization cascade reaction of 3-chlorooxindoles with 2,3-dioxopyrrolidines produced the corresponding chiral spiro-compounds in high yields with excellent stereoselectivities.

Cited by 18 publications

References 31 publications

Asymmetric Addition and Cycloaddition Reactions with Ylidene‐Five‐Membered Heterocycles

Asymmetric Addition and Cycloaddition Reactions with Ylidene‐Five‐Membered Heterocycles

Regiodivergent Organocatalytic Reactions

Recent Advances in Squaramide-Catalyzed Asymmetric Cascade Reactions for the Synthesis of Spirooxindoles

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