Tetrahedron

Substitution reactions of 2-phenylsulphonyl-piperidines and-pyrrolidines with carbon nucleophiles: Synthesis of the pyrrolidine alkaloids norruspoline and ruspolinone

DS Brown, P Charreau, T Hansson, SV Ley

Index: Brown, Dearg S.; Charreau, Philippe; Hansson, Thomas; Ley, Steven V. Tetrahedron, 1991 , vol. 47, # 7 p. 1311 - 1328

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Citation Number: 81

Abstract

Several 2-phenylsulphonyl-piperidines and-pyrrolidines were prepared from the corresponding N-acyl aminals by treatment with benzenesulphinic acid. On reaction with various carbon nucleophiles these sulphones gave good yields of substitution products. Typical nucleophiles used in these studies were organometallic reagents derived from Grignard reagents and zinc halide together with silyl enol ethers, silyl ketene acetals, ...