Ruthenium-catalyzed cycloaddition of nitrile oxides and alkynes: Practical synthesis of isoxazoles

Abstract

(Chemical Equation Presented) 3,4-Disubstituted and 3,4,5-trisubstituted isoxazoles have been formed from alkynes and nitrile oxides in a ruthenium(II)-catalyzed process (see scheme; cod=cycloocta-l,5-diene, Cp*=C₅Me₅). These reactions are experimentally simple, proceed at room temperature, and produce isoxazoles with excellent regioselectivity in high yield.

Original language	English
Pages (from-to)	8285-8287
Number of pages	3
Journal	Angewandte Chemie - International Edition
Volume	47
Issue number	43
DOIs	https://doi.org/10.1002/anie.200801920
Publication status	Published - 13 Oct 2008
Externally published	Yes

Keywords

Cycloaddition
Homogeneous catalysis
Isoxazoles
Nitrile oxides
Ruthenium

ASJC Scopus subject areas

Chemistry(all)
Catalysis

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10.1002/anie.200801920

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title = "Ruthenium-catalyzed cycloaddition of nitrile oxides and alkynes: Practical synthesis of isoxazoles",

abstract = "(Chemical Equation Presented) 3,4-Disubstituted and 3,4,5-trisubstituted isoxazoles have been formed from alkynes and nitrile oxides in a ruthenium(II)-catalyzed process (see scheme; cod=cycloocta-l,5-diene, Cp*=C5Me5). These reactions are experimentally simple, proceed at room temperature, and produce isoxazoles with excellent regioselectivity in high yield.",

keywords = "Cycloaddition, Homogeneous catalysis, Isoxazoles, Nitrile oxides, Ruthenium",

author = "Scott Grecian and Fokin, {Valery V.}",

year = "2008",

month = oct,

day = "13",

doi = "10.1002/anie.200801920",

language = "English",

volume = "47",

pages = "8285--8287",

journal = "Angewandte Chemie - International Edition",

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publisher = "John Wiley and Sons Ltd",

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}

TY - JOUR

T1 - Ruthenium-catalyzed cycloaddition of nitrile oxides and alkynes

T2 - Practical synthesis of isoxazoles

AU - Grecian, Scott

AU - Fokin, Valery V.

PY - 2008/10/13

Y1 - 2008/10/13

N2 - (Chemical Equation Presented) 3,4-Disubstituted and 3,4,5-trisubstituted isoxazoles have been formed from alkynes and nitrile oxides in a ruthenium(II)-catalyzed process (see scheme; cod=cycloocta-l,5-diene, Cp*=C5Me5). These reactions are experimentally simple, proceed at room temperature, and produce isoxazoles with excellent regioselectivity in high yield.

AB - (Chemical Equation Presented) 3,4-Disubstituted and 3,4,5-trisubstituted isoxazoles have been formed from alkynes and nitrile oxides in a ruthenium(II)-catalyzed process (see scheme; cod=cycloocta-l,5-diene, Cp*=C5Me5). These reactions are experimentally simple, proceed at room temperature, and produce isoxazoles with excellent regioselectivity in high yield.

KW - Cycloaddition

KW - Homogeneous catalysis

KW - Isoxazoles

KW - Nitrile oxides

KW - Ruthenium

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DO - 10.1002/anie.200801920

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