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

Zsanett Benke, Melinda Nonn, F. Fülöp, L. Kiss

Research output: Article

Abstract

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 cycloalkene-fused isoxazoline products were easily converted through ring opening and cross metathesis into valuable dialkenylated heterocycles.

Original languageEnglish
Pages (from-to)2886-2891
Number of pages6
JournalChemistrySelect
Volume4
Issue number10
DOIs
Publication statusPublished - márc. 14 2019

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Nitriles
Cycloaddition
Alkenes
Oxides
Cycloparaffins
Regioselectivity

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

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title = "An Insight into Selective Olefin Bond Functionalization of Cyclodienes through Nitrile Oxide 1,3-Dipolar Cycloadditions",
abstract = "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 cycloalkene-fused isoxazoline products were easily converted through ring opening and cross metathesis into valuable dialkenylated heterocycles.",
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author = "Zsanett Benke and Melinda Nonn and F. F{\"u}l{\"o}p and L. Kiss",
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T1 - An Insight into Selective Olefin Bond Functionalization of Cyclodienes through Nitrile Oxide 1,3-Dipolar Cycloadditions

AU - Benke, Zsanett

AU - Nonn, Melinda

AU - Fülöp, F.

AU - Kiss, L.

PY - 2019/3/14

Y1 - 2019/3/14

N2 - 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 cycloalkene-fused isoxazoline products were easily converted through ring opening and cross metathesis into valuable dialkenylated heterocycles.

AB - 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 cycloalkene-fused isoxazoline products were easily converted through ring opening and cross metathesis into valuable dialkenylated heterocycles.

KW - Cycloaddition

KW - isoxazoline

KW - metathesis

KW - nitrile oxide

KW - selectivity

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