Tetrahedron

Radical cyclization in heterocycle synthesis. Part 13: Sulfanyl radical addition–cyclization of oxime ethers and hydrazones connected with alkenes for synthesis of …

…, T Kobayashi, R Yamanaka, S Kajisa, J Koide, T Naito

Index: Miyata, Okiko; Muroya, Kanami; Kobayashi, Tomoko; Yamanaka, Rina; Kajisa, Seiko; Koide, Junko; Naito, Takeaki Tetrahedron, 2002 , vol. 58, # 22 p. 4459 - 4479

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Citation Number: 50

Abstract

A combination of sulfanyl radical addition–cyclization of the oxime ethers and hydrazones connected with alkenes and subsequent conversion of a phenylsulfanylmethyl group to a carboxyl group provides a novel method for the construction of the cyclic β-amino acids. Upon treatment with thiophenol in the presence of AIBN, the oxime ethers and hydrazones smoothly underwent sulfanyl radical addition-cyclization to give the 2-( ...