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5.2.24.5.3 Variation 3: Using 1,3-Cycloadditions of Alkynylstannanes

DOI: 10.1055/sos-SD-005-00476

Crisp, G. T.Science of Synthesis, (20035510.

1,3-Dipolar cycloaddition reactions of alkynyltrimethylsilanes with nitrile oxides give 3-substituted 5-(trimethylstannyl)isoxazoles 33 and 3,5-disubstituted 4-(trimethylstannyl)isoxazoles 32 in modest to good yields, depending on the substituents on the fulminates and on the alkyne (Scheme 13).[‌6‌] 3-Phenyl- and 3-(ethoxycarbonyl)-5-(trimethylstannyl)isoxazoles 33 are not stable towards attempted purification on silica gel and are destannylated to give the corresponding 3-substituted isoxazoles (R1 = Ph, EtOC(O) as 34). The 3,5-disubstituted 4-(trimethylstannyl)isoxazoles are formed regioselectively and these derivatives are stable on silica gel.

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