Journal ArticleDOI
Stereo-, Regio-, and Chemoselective [3 + 2]-Cycloaddition of (2E,4E)-Ethyl 5-(Phenylsulfonyl)penta-2,4-dienoate with Various Azomethine Ylides, Nitrones, and Nitrile Oxides: Synthesis of Pyrrolidine, Isoxazolidine, and Isoxazoline Derivatives and a Computational Study
Ulaganathan Sankar,Ch. Venkata Surya Kumar,Venkatesan Subramanian,Kalpattu K. Balasubramanian,S. Mahalakshimi +4 more
TLDR
One-pot chemo-, regio-, and stereoselective synthesis of series of heterocyclic and spiroheterocyclIC compounds was accomplished through mono- and bis[3 + 2]-cycloaddition reactions of (2E,4E)-ethyl 5-(phenylsulfonyl)penta-2,4-dienoate as a dipolarophile with azomethine ylides, nitrones, and nitrile oxidesAbstract:
One-pot chemo-, regio-, and stereoselective synthesis of series of heterocyclic and spiroheterocyclic compounds was accomplished through mono- and bis[3 + 2]-cycloaddition reactions of (2E,4E)-ethyl 5-(phenylsulfonyl)penta-2,4-dienoate as a dipolarophile with azomethine ylides, nitrones, and nitrile oxides in good yields. The structures of the products were established by spectroscopic techniques as well as by single-crystal XRD study, and DFT calculations were performed to further understand the mechanism of this [3 + 2]-cycloaddition reaction.read more
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Asymmetric synthesis of chiral oxindoles using isatin as starting material
TL;DR: This review makes a detailed overview of the latest developments in the use of isatin as starting material for the asymmetric synthesis of spirooxindoles and 3,3-disubstituted oxindoles during the period from 2015 to 2017.
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A mild light-induced cleavage of the S–O bond of aryl sulfonate esters enables efficient sulfonylation of vinylarenes
TL;DR: A new mode of S–O bond activation has been discovered, which constitutes novel reactivity of easily available and bench-stable arylsulfonate phenol esters, which enables straightforward access to valuable vinyl sulfones.
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Tandem Aryne-Capture/Sigmatropic Rearrangement as a Metal-Free Entry to Functionalized N-Aryl Pyrrolidines.
TL;DR: A tandem aryne-capture/anion isomerisation/[2,3]-sigmatropic rearrangement is induced, leading to good yields of 3-substituted N-aryl-2-acylpyrrolidines, known subunits of biological probes, sensors and drug-like fragments, and not easily accessed directly by other methods.
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Understanding the reactivity and regioselectivity of [3 + 2] cycloaddition reactions between substituted nitrile oxides and methyl acrylate. A molecular electron density theory study
Ibrahim Mbouombouo Ndassa,Abel Idrice Adjieufack,Joseph Mbadcam Ketcha,Slawomir Berski,Mar Ríos-Gutiérrez,Luis R. Domingo +5 more
TL;DR: In this paper, topological analysis of the electron localization function of these NOs permits to establish that they will participate in zw-type cycloaddition (32CA) reactions.
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Stereo- and Regioselective 1,3-Dipolar Cycloaddition of the Stable Ninhydrin-Derived Azomethine Ylide to Cyclopropenes: Trapping of Unstable Cyclopropene Dipolarophiles
Alexander S. Filatov,Siqi Wang,Olesya V. Khoroshilova,Stanislav V. Lozovskiy,Anna G. Larina,Vitali M. Boitsov,Alexander V. Stepakov,Alexander V. Stepakov +7 more
TL;DR: New approaches provide a straightforward strategy for the synthesis of functionally substituted cyclopropa[ a]pyrrolizine derivatives, and the factors governing regio- and stereoselectivity have been revealed by means of quantum mechanical calculations (M11 density functional theory), including previously unreported Nylide- Hcyclopropene second-orbital interactions.
References
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