ChemInform Abstract: AZOLE, REAKTIVITAET VON 2‐METHYL‐2‐ISOXAZOLINIUMSALZEN, SYNTHESE VON 3‐ISOXAZOLINEN

Belly, Alain; Petrus, C.; Petrus, Francoise

doi:10.1002/chin.197437255

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“…Surprisingly, this potential has largely been neglected concerning isoxazolinium salts, since there have been few relevant reports (altogether, until 2008, we have found less than 30 papers in the literature dealing with isoxazolinium salts!). There are scattered examples where sodium borohydride [20, 24 -26], lithium aluminium hydride [27], methyl and phenyl Grignard reagents [26], methoxide [28], and diphenyl phosphite [21] have been employed for such additions (Scheme 5).…”

Section: -Isoxazolinium Saltsmentioning

confidence: 99%

2-Isoxazolinium Salts and 3-Isoxazolines: Exploratory Chemistry and Uses for the Synthesis of Branched Amino Polyols and Amino Acids

Jäger

Frey

Bathich

et al. 2010

Zeitschrift Für Naturforschung B

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Dedicated to Professor Alessandro Dondoni on the occasion of his 75 th birthday2-Isoxazolines represent a well known class of heterocycles, readily accessible in particular by 1,3-dipolar cycloaddition of nitrile oxides to alkenes. 2-Isoxazolines are easily transformed into 2-isoxazolinium salts by N-methylation, and further into 3-isoxazolines by deprotonation. In contrast to the parent system, less is known concerning the chemistry of the derived classes, and potential applications in synthesis. -2-Isoxazolinium salts, due to their iminium part, are prone to the attack of nucleophiles, and examples for this, addition of hydride (reduction) and C-nucleophiles like methylmagnesium bromide, cyanide, methane nitronate, and malonate are given. With these adducts, syntheses of β -and α-amino acids with OH-containing side chains have been effected. The cyanide products also are useful as precursors of branched, unsymmetrical 1,2-diamino polyols. -On the other hand, 3-isoxazolines due to their oxy-enamine part, represent species with nucleophilic sites and therefore react with electrophilic reagents. Examples given are [3+2] cycloadditions with nitrile oxides, [2+2] cycloadditions with dimethyl acetylenedicarboxylate, and [2+1] cycloaddition in the form of epoxidation which, however, led to a dihydro-1,3-oxazine nitrone by initial attack at the nitrogen atom, in an unprecedented oxidation/N-dealkylation/rearrangement sequence.

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Section: -Isoxazolinium Saltsmentioning

confidence: 99%

2-Isoxazolinium Salts and 3-Isoxazolines: Exploratory Chemistry and Uses for the Synthesis of Branched Amino Polyols and Amino Acids

Jäger

Frey

Bathich

et al. 2010

Zeitschrift Für Naturforschung B

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ChemInform Abstract: AZOLE, REAKTIVITAET VON 2‐METHYL‐2‐ISOXAZOLINIUMSALZEN, SYNTHESE VON 3‐ISOXAZOLINEN

Abstract: Aus den Arylisoxazoliniumperchloraten (I) entstehen unter der Einwirkung von wäl Iigem Na2CO3 bei 10°C (analog auch bei der Behandlung mit methanolischem Na‐methylat bei ‐20°C) über die Stufe der Addukte (II) die Arylisoxazoline (III).

Cited by 1 publication

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2-Isoxazolinium Salts and 3-Isoxazolines: Exploratory Chemistry and Uses for the Synthesis of Branched Amino Polyols and Amino Acids

2-Isoxazolinium Salts and 3-Isoxazolines: Exploratory Chemistry and Uses for the Synthesis of Branched Amino Polyols and Amino Acids

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