Tetrahedron

Novel synthesis of substituted pyrrolidines and piperidines via radical addition–ionic cyclization reaction of oxime ethers

O Miyata, S Takahashi, A Tamura, M Ueda, T Naito

Index: Miyata, Okiko; Takahashi, Shinya; Tamura, Akira; Ueda, Masafumi; Naito, Takeaki Tetrahedron, 2008 , vol. 64, # 7 p. 1270 - 1284

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Citation Number: 25

Abstract

We have developed a novel synthetic route to nitrogen-containing heterocycles via radical addition–ionic cyclization reaction. Treatment of oxime ethers carrying the tosyloxy group with Et3B and alkyl iodide in the presence of Lewis acid gave the substituted pyrrolidines and piperidines. The reaction of oxime ethers carrying the methoxycarbonyl group proceeded under the same conditions to give the amino esters, which were easily ...