7 research outputs found

    Synthesis and Asymmetric Resolution of α‑Azido-peroxides

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    An unprecedented synthesis of α-azido-peroxides has been developed using an FeCl<sub>3</sub>-catalyst starting from carbonyl, TMS-azide, and hydroperoxide. Further, a base promoted decomposition of synthesized secondary α-azido-peroxides to provide the corresponding <i>tert</i>-butyl esters has been disclosed. Finally, an asymmetric kinetic resolution of such α-azido-peroxides has also been developed to provide chiral α-azido-peroxides in excellent enantiopurity

    Trapping of Azidocarbenium Ion: A Unique Route for Azide Synthesis

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    For the first time, a sensitive azidocarbenium ion intermediate has been trapped with various nucleophiles to provide azides in excellent chemoselectivity. This provides a novel approach for the chemoselective synthesis of primary and secondary benzyl azides from aldehydes in a one-pot reaction. Enantioselective nucleophilic addition to the azidocarbenium ion has also been initiated

    Synthesis and Asymmetric Resolution of α‑Azido-peroxides

    No full text
    An unprecedented synthesis of α-azido-peroxides has been developed using an FeCl<sub>3</sub>-catalyst starting from carbonyl, TMS-azide, and hydroperoxide. Further, a base promoted decomposition of synthesized secondary α-azido-peroxides to provide the corresponding <i>tert</i>-butyl esters has been disclosed. Finally, an asymmetric kinetic resolution of such α-azido-peroxides has also been developed to provide chiral α-azido-peroxides in excellent enantiopurity

    Trapping of Azidocarbenium Ion: A Unique Route for Azide Synthesis

    No full text
    For the first time, a sensitive azidocarbenium ion intermediate has been trapped with various nucleophiles to provide azides in excellent chemoselectivity. This provides a novel approach for the chemoselective synthesis of primary and secondary benzyl azides from aldehydes in a one-pot reaction. Enantioselective nucleophilic addition to the azidocarbenium ion has also been initiated

    Intramolecular Rearrangement of α‑Azidoperoxides: An Efficient Synthesis of <i>tert</i>-Butyl Esters

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    An unprecedented intramolecular rearrangement of α-azidoperoxides, promoted by simple organic base to provide <i>tert</i>-butyl esters, has been presented. Further, a one-pot methodology consisting of in situ generation of the α-azidoperoxides from corresponding aldehydes followed by base-promoted rearrangement to obtain the desired ester has also been executed. Relevant mechanistic studies, to provide the proof for intramolecular alkoxy transfer, are investigated

    Organosilicon Reducing Reagents for Stereoselective Formations of Silyl Enol Ethers from α‑Halo Carbonyl Compounds

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    Salt-free stereoselective synthesis of silyl enol ethers was achieved by treating α-halo carbonyl compounds with 2,3,5,6-tetramethyl-1,4-bis­(trimethylsilyl)-1,4-dihydropyrazine. In this reaction, easily removable trimethylsilyl halides and 2,3,5,6-tetramethylpyrazine were generated as the reaction byproducts. Due to the inertness of the reaction byproducts, we found a one-pot transformation of the <i>in situ</i> generated silyl enol ethers into various α-functionalized carbonyls by reaction with Togni-II reagent or aldehydes

    Organocatalytic Enantioselective Intramolecular Oxa-Michael Reaction of Enols: Synthesis of Chiral Isochromenes

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    An unprecedented enantioselective intramolecular oxa-Michael reaction of enols has been described. A squaramide-containing tertiary amine based bifunctional organocatalyst efficiently activates the <i>o</i>-homoformyl chalcones to provide the chiral isochromenes in moderate yields and good to excellent enantioselectivities. Further, late-stage functionalizations of the vinyl ether moiety of the chiral isochromene products have also been exemplified
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