Ring-opening metathesis of some strained bicyclic systems; stereocontrolled access to diolefinated saturated heterocycles with multiple stereogenic centers

Benke, Zsanett; Nonn, Melinda; Kardos, Márton; Fustero, Santos; Kiss, Lóránd

doi:10.3762/bjoc.14.247

Cited by 10 publications

(20 citation statements)

References 36 publications

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“…Dialkenylated isoxazoline 20 was derived from 16 a by ROM with Hoveyda‐Grubbs 1 st generation catalyst, according to our procedure described earlier . Product 20 was subjected to CM with two unsaturated reagents, namely methyl acrylate and butanone.…”

Section: Resultsmentioning

confidence: 99%

An Insight into Selective Olefin Bond Functionalization of Cyclodienes through Nitrile Oxide 1,3‐Dipolar Cycloadditions

et al. 2019

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Selective functionalizations of the ring olefin bond of various commercial cyclodienes through nitrile oxide dipolar cycloaddition is described. Nitrile oxides were generated from primary nitroalkanes by Mukaiyama's method. Besides regioselectivity, the dipolar cycloadditions have been performed in view of selectivity of the ring olefin bonds. The cycloalkenefused isoxazoline products were easily converted through ring opening and cross metathesis into valuable dialkenylated heterocycles.

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Section: Resultsmentioning

confidence: 99%

An Insight into Selective Olefin Bond Functionalization of Cyclodienes through Nitrile Oxide 1,3‐Dipolar Cycloadditions

et al. 2019

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“…Electronic or steric factors, chelation effects, and intramolecular H-bonding interaction in the intermediate may affect the outcome of the reaction. 33…”

Section: Scheme 17 Vince's Lactam Transformation Through Rommentioning

confidence: 99%

Diversity-Oriented Synthesis of Highly Functionalized Alicycles across Dipolar Cycloaddition/Metathesis Reaction

Kiss

Benke

Nonn

et al. 2021

Synlett

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This Account gives an insight into the selective functionalization of some readily available commercial cyclodienes across simple chemical transformations into functionalized small-molecular scaffolds. The syntheses involved selective cycloadditions, followed by ring-opening metathesis (ROM) of the resulting azetidin-2-one derivatives or isoxazoline frameworks and selective cross metathesis (CM) by discrimination of the C=C bonds on the alkenylated heterocycles. The CM protocols have been described when investigated under various conditions with the purpose on exploring chemodifferentiation of the olefin bonds and a study on the access of the corresponding functionalized β-lactam or isoxazoline derivatives is presented. Due to the expanding importance of organofluorine chemistry in drug research as well as of the high biological potential of β-lactam derivatives several illustrative examples to the access of some fluorine-containing molecular entities is also presented in this synopsis.1 Introduction2 Ring C=C Bond Functionalization of Some Cycloalkene β-Amino Acid Derivatives across Chlorosulfonyl Isocyanate Cycloaddition3 Ring C=C Bond Functionalization of Some Cycloalkene β-Amino Acid Derivatives across Nitrile Oxide Cycloaddition4 Ring C=C Bond Functionalization of Some Cycloalkene β-Amino Acid Derivatives across Metathesis5 Functionalization of sSome Cyclodienes across Nitrile Oxide Cycloaddition6 Selective Synthesis of Functionalized Alicycles across Ring-Opening Metathesis7 Selective Synthesis of Functionalized Alicycles through Cross Metathesis8 Summary and Outlook9 List of Abbreviations

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“…Compound (�)-42, when reacted with methyl vinyl ketone or methyl acrylate in the presence of HG-2, led to dicoupled derivatives (�)-43 and (�)-44 in a CM reaction (Scheme 11). [14]…”

Section: Functionalizations By Rom/cm Of Cycloalkene-fused Isoxazolinmentioning

confidence: 99%

“…For this reason, 1,5cyclooctadiene the selected starting model compound was converted through selective nitrile oxide cycloaddition into cyclooctene-fused isoxazoline (�)-41 which, in turn, afforded dialkenylated izoxazoline (�)-42 by ring-opening metathesis (ROM). [14] Our aim was to convert compound (�)-42 into novel functionalized scaffolds and to study the chemical behavior of practically equivalent olefin bonds in (�)-42 under CM transformations. Hereby, in this section some preliminary results will be briefly presented.…”

Section: Functionalizations By Rom/cm Of Cycloalkene-fused Isoxazolinmentioning

confidence: 99%

Diversity‐oriented Functionalization of Cyclodienes Through Selective Cycloaddition/Ring‐opening/Cross‐metathesis Protocols; Transformation of a “Flatland” into Three‐dimensional Scaffolds With Stereo‐ and Regiocontrol

Kiss

Benke

Remete

et al. 2020

The Chemical Record

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This article presents selective transformations of some readily available cyclodienes through simple chemical procedures into novel functionalized small-molecular entities. The syntheses hereby described involved selective cycloadditions, followed by ring-opening metathesis of the resulting β-lactam or isoxazoline derivatives and selective cross-metathesis by differentiation of the olefin bonds on the alkenylated heterocycles. The cross-metathesis transformations have been detailed, which were performed under various experimental conditions with the aim of exploring chemodiscrimination of the olefin bonds and delivering the corresponding functionalized β-lactam or isoxazoline derivatives.

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Ring-opening metathesis of some strained bicyclic systems; stereocontrolled access to diolefinated saturated heterocycles with multiple stereogenic centers

Cited by 10 publications

References 36 publications

An Insight into Selective Olefin Bond Functionalization of Cyclodienes through Nitrile Oxide 1,3‐Dipolar Cycloadditions

An Insight into Selective Olefin Bond Functionalization of Cyclodienes through Nitrile Oxide 1,3‐Dipolar Cycloadditions

Diversity-Oriented Synthesis of Highly Functionalized Alicycles across Dipolar Cycloaddition/Metathesis Reaction

Diversity‐oriented Functionalization of Cyclodienes Through Selective Cycloaddition/Ring‐opening/Cross‐metathesis Protocols; Transformation of a “Flatland” into Three‐dimensional Scaffolds With Stereo‐ and Regiocontrol

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