The exhaustive silylation of 5-nitro-pentan-2-one: novel processes and opportunities

AA Tishkov, SL Ioffe, YA Strelenko, VA Tartakovsky

Index: Tishkov, Alexander A.; Lyapkalo, Il'ya M.; Ioffe, Sema L.; Strelenko, Yuri A.; Tartakovsky, Vladimir A. Tetrahedron, 2001 , vol. 57, # 11 p. 2221 - 2230

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Citation Number: 6

Abstract

Treatment of 5-nitro-pentan-2-one (1) with Me3SiOTf/Et3N leads to initial silylation of the C (O) Me-group to give regioisomeric silyl enol ethers 2a and 2b followed by double silylation of the NO2-group furnishing a mixture of N, N-bis (silyloxy) enamine 4a and enoxime TMS ether 6. Employment of a large excess of Me3SiOTf/Et3N triggers a cascade of eliminations and silylations to give a mixture of (E)-4-trimethylsilyloxy-2-trimethylsilyl-pent-2, 4- ...