Enantioselective synthesis of functionalized 1,4-dihydropyrazolo-[4′,3′:5,6]pyrano[2,3-<i>b</i>]quinolines through ferrocenyl-phosphine-catalyzed annulation of modified MBH carbonates and pyrazolones

Xiao, Xiao; Shao, Bingxuan; Li, Jingyi; Yang, Zehui; Lu, Yin‐Jie; Ling, Fei; Zhong, Weihui

doi:10.1039/d1cc00989c

Cited by 18 publications

(7 citation statements)

References 47 publications

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“…Although great progress has been achieved in this field, the core framework of MBH carbonates is monotonous and limited to the classical MBH adducts from aldehyde (Scheme A) and isatins (Scheme B). Accordingly, development of structurally diverse MBH carbonates is needed …”

Section: Introductionmentioning

confidence: 99%

Organocatalytic Regio- and Enantioselective [3 + 2]-Annulations of Ninhydrin-Derived Morita–Baylis–Hillman Carbonates with 3-Methyleneoxindoles

Jia

Chen

et al. 2022

J. Org. Chem.

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A type of Morita−Baylis−Hillman (MBH) carbonates has been developed from ninhydrin. These MBH carbonates have been successfully employed as 3C-synthons in the organocatalytic asymmetric [3 + 2]-annulations of the isatin-derived electron-deficient olefins, affording structurally diverse spirooxindoles in high yield with excellent stereoselectivity. In particular, the regioselectivity of MBH carbonates was controlled by the reaction partner, 3-methyleneoxindoles with carbonyl groups (R = ArCO), affording β-selective products and 3-methyleneoxindoles with ester groups (R = CO 2 Me) furnishing γ-selective products. The representative scale-up reactions and transformation of product were examined. The reaction mechanism was expounded by control experiments.

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Section: Introductionmentioning

confidence: 99%

Organocatalytic Regio- and Enantioselective [3 + 2]-Annulations of Ninhydrin-Derived Morita–Baylis–Hillman Carbonates with 3-Methyleneoxindoles

Jia

Chen

et al. 2022

J. Org. Chem.

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“…Very recently, based on previous work (Scheme 2), 12 fixing a leaving group on the ortho -position of the MBH carbonate allowed the same catalytic system to support the enantioselective (3 + 3) annulation of pyrazolones 1 and modified MBH carbonates 30 (Scheme 6). 19 The ring-fused pyrazole derivatives 31 , featuring pharmaceutically important quinoline moieties, were then furnished in moderate to high yields with excellent enantioselectivities. Moreover, to further emphasize the significance of this protocol, the cytotoxic properties of the products were investigated.…”

Section: -Non-substituted Pyrazolone As a Synthonmentioning

confidence: 99%

Recent advances in the applications of pyrazolone derivatives in enantioselective synthesis

et al. 2022

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“…Organocatalysis, designed to mimic biomimetic catalysis, is a powerful instrument by which to fulfill fascinating transformations [ 62 , 63 , 64 , 65 , 66 , 67 , 68 , 69 ]. To date, nucleophilic catalysis has experienced a range of developments regarding the construction of C–N axially chiral compounds by utilizing chiral amines [ 70 , 71 , 72 , 73 , 74 ] or isothioureas [ 75 , 76 ] as catalysts.…”

Section: Enantioselective Synthesis Of Acyclic C–n Axially Chiral Amidesmentioning

confidence: 99%

Construction of Non-Biaryl Atropisomeric Amide Scaffolds Bearing a C–N Axis via Enantioselective Catalysis

et al. 2022

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The significant scaffold offered by atropisomeric amides with a C–N chiral axis has been extensively utilized for pharmaceuticals, agricultural science, and organic syntheses. As a result, the field of atropisomer synthesis has attracted considerable interest within chemistry communities. To date, a range of catalytic atroposelective approaches has been reported for the efficient construction of these challenging scaffolds. However, greatly concise and highly useful methodologies for the synthesis of these atropisomeric compounds, focusing on transition-metal, chiral amine, and phosphoric acid catalysis reactions, etc., are still desirable. Hence, it is indispensable to succinctly and systematically present all such reports by means of disclosing the mechanistic analysis and application, as well as the challenges and issues associated with the establishment of these atropisomers. In this review, we summarize the development of catalytic asymmetric synthetic strategies to access non-biaryl atropisomers rotating around a C–N chiral axis, including the reaction methods, mechanism, late-stage transformations, and applications.

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Enantioselective synthesis of functionalized 1,4-dihydropyrazolo-[4′,3′:5,6]pyrano[2,3-b]quinolines through ferrocenyl-phosphine-catalyzed annulation of modified MBH carbonates and pyrazolones

Cited by 18 publications

References 47 publications

Organocatalytic Regio- and Enantioselective [3 + 2]-Annulations of Ninhydrin-Derived Morita–Baylis–Hillman Carbonates with 3-Methyleneoxindoles

Organocatalytic Regio- and Enantioselective [3 + 2]-Annulations of Ninhydrin-Derived Morita–Baylis–Hillman Carbonates with 3-Methyleneoxindoles

Recent advances in the applications of pyrazolone derivatives in enantioselective synthesis

Construction of Non-Biaryl Atropisomeric Amide Scaffolds Bearing a C–N Axis via Enantioselective Catalysis

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