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New Strategy for the Synthesis of 3,4,5-trisubstituted Isoxazolines from Allyl Compounds

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A new strategy for the synthesis of trans- and cis + trans-3,4,5-trisubstituted isoxazolines from allyl compounds of QCH2CH=CH2 type (Q = PhO, 2,2’-bithiophen-5-yl, BuO, Me3CS, PhN(COMe) and others) has been developed. The dipolarophiles are prepared via: a) Ru-carbene catalysed metathesis of Qallyl; b) catalytic isomerization followed by Ru-carbene mediated metathesis; c) Ru-carbene catalysed metathesis followed by isomerization. 1,3-dipolar cycloaddition of nitrile oxide to dipolarophiles obtained via route a), b) or c), including high pressure activated reactions leads to 3,4,5-trisubstituted isoxazolines. Quantitative E-stereoselective homometathesis of some QCH2CH=CH2 to (E)-QCH2CH=CHCH2Q and new highly effective ruthenium and basic catalytic systems for the isomerization of allyl compounds have also been presented. Moreover, easily available (Z)-XCH2CH=CHCH2X allyl compounds were used for the synthesis of cis-3,4,5-trisubstituted isoxazolines. It has been proved by in vitro tests that some of the isoxazolines show interesting antifungal activity comparable to that of fluconazole.
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Keywords: 1; 3-Dipolar Cycloaddition; Antifungal agents; High-pressure chemistry; Homogeneous catalysis; Isomerization; Isoxazolines; Metathesis; Regioselectivity

Document Type: Research Article

Publication date: September 1, 2014

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