Phosphine‐Initiated Domino Reaction: A Convenient Method for the Preparation of Spirocyclopentanones

Liang, Ling; Li, Erqing; Xie, Peizhong; Huang, You

doi:10.1002/asia.201301641

Cited by 49 publications

(15 citation statements)

References 69 publications

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“…In 2012, the Shi group and the Huang group explored the phosphane‐catalyzed [3+2] annulation of ynones with isatins, affording spiro[furan‐2,3′‐indoline]‐2′,4(5 H )‐diones 3,4. The Huang group presented a phosphane‐catalyzed [3+2] annulation reaction of ynones and 2‐arylideneindane‐1,3‐diones for the construction of spirocyclopentanone skeletons 5. In 2013, Ramachary and co‐workers achieved a phosphane‐catalyzed Tomiat–Zipper cyclization of methyleneoxindoles with 4‐phenylbut‐3‐yn‐2‐one, providing functionalized five‐membered spirooxindoles 6.…”

Section: Methodsmentioning

confidence: 99%

Binding to Large Enzyme Pockets: Small‐Molecule Inhibitors of Trypanothione Reductase

et al. 2014

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The causative agents of the parasitic disease human African trypanosomiasis belong to the family of trypanosomatids. These parasitic protozoa exhibit a unique thiol redox metabolism that is based on the flavoenzyme trypanothione reductase (TR). TR was identified as a potential drug target and features a large active site that allows a multitude of possible ligand orientations, which renders rational structure-based inhibitor design highly challenging. Herein we describe the synthesis, binding properties, and kinetic analysis of a new series of small-molecule inhibitors of TR. The conjunction of biological activities, mutation studies, and virtual ligand docking simulations led to the prediction of a binding mode that was confirmed by crystal structure analysis. The crystal structures revealed that the ligands bind to the hydrophobic wall of the so-called "mepacrine binding site". The binding conformation and potency of the inhibitors varied for TR from Trypanosoma brucei and T. cruzi.

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Section: Methodsmentioning

confidence: 99%

Binding to Large Enzyme Pockets: Small‐Molecule Inhibitors of Trypanothione Reductase

et al. 2014

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“…To further expand the area of Michael– α -umpolung annulation, the Huang group used arylideneindan-1,3-diones as reaction partners to produce a collection of functionalized spiroindan-1,3-diones in good yields (Scheme 475). 546 The reaction tolerates arylideneindan-1,3-diones bearing various substituents (e.g., m -bromophenyl, o -tolyl, and p -nitrophenyl groups) while maintaining good efficiencies. With a strongly electron-withdrawing nitro group, however, the yield decreased slightly.…”

Section: Nucleophilic Phosphine Catalysis Of Acetylenesmentioning

confidence: 99%

Phosphine Organocatalysis

et al. 2018

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The hallmark of nucleophilic phosphine catalysis is the initial nucleophilic addition of a phosphine to an electrophilic starting material, producing a reactive zwitterionic intermediate, generally under mild conditions. In this Review, we classify nucleophilic phosphine catalysis reactions in terms of their electrophilic components. In the majority of cases, these electrophiles possess carbon–carbon multiple bonds: alkenes (section 2), allenes (section 3), alkynes (section 4), and Morita–Baylis–Hillman (MBH) alcohol derivatives (MBHADs; section 5). Within each of these sections, the reactions are compiled based on the nature of the second starting material—nucleophiles, dinucleophiles, electrophiles, and electrophile–nucleophiles. Nucleophilic phosphine catalysis reactions that occur via the initial addition to starting materials that do not possess carbon–carbon multiple bonds are collated in section 6. Although not catalytic in the phosphine, the formation of ylides through the nucleophilic addition of phosphines to carbon–carbon multiple bond–containing compounds is intimately related to the catalysis and is discussed in section 7. Finally, section 8 compiles miscellaneous topics, including annulations of the Hüisgen zwitterion, phosphine-mediated reductions, iminophosphorane organocatalysis, and catalytic variants of classical phosphine oxide–generating reactions.

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“…[3,4] TheH uang group presented ap hosphane-catalyzed [3+ +2] annulation reactiono f ynones and 2-arylideneindane-1,3-diones for the construction of spirocyclopentanone skeletons. [5] In 2013, Ramachary and co-workers achieved ap hosphanecatalyzed Tomiat-Zipper cyclization of methyleneoxindolesw ith 4-phenylbut-3-yn-2-one,p roviding functionalized five-membered spirooxindoles. [6] Most recently,D ud eveloped phosphane-promoted [ 4 + +2] annulation reactions of unsaturated pyrazolones with but-3-yn-2-one and [3+ +2] annulation reactions of unsaturatedp yrazolones with 4-phenylbut-3-yn-2-one, providing pyrano [2,3-c]pyrazoles and spirocyclopentanonepyrazolones.…”

mentioning

confidence: 99%

Phosphane‐Catalyzed [3+3] Annulation of C,N‐Cyclic Azomethine Imines with Ynones: A Practical Method for Tricyclic Dinitrogen‐Fused Heterocycles

Yang

et al. 2016

Adv Synth Catal

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Ap hosphane-catalyzed [3+ +3] annulation of azomethine imines with ynones has been developed. Under mild reactionc onditions,t he reaction proceeds smoothly to affordt ricyclic dinitrogenfused heterocyclic compoundsi nm oderate to excellent yields with moderate to excellent stereoselectivies.U sing ac hiral phosphinea st he catalyst, the reaction could worktog ive the cycloadduct in moderate yield with moderate enantioselectivity.

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Phosphine‐Initiated Domino Reaction: A Convenient Method for the Preparation of Spirocyclopentanones

Abstract: An efficient synthetic approach has been developed for the construction of the spirocyclopentanone skeleton via a phosphine-catalyzed [3+2] annulation reaction. With this novel and economical protocol, various quaternary carbon-centered spirocyclopentanones could be readily obtained.

Cited by 49 publications

References 69 publications

Binding to Large Enzyme Pockets: Small‐Molecule Inhibitors of Trypanothione Reductase

Binding to Large Enzyme Pockets: Small‐Molecule Inhibitors of Trypanothione Reductase

Phosphine Organocatalysis

Phosphane‐Catalyzed [3+3] Annulation of C,N‐Cyclic Azomethine Imines with Ynones: A Practical Method for Tricyclic Dinitrogen‐Fused Heterocycles

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