Direct Substitution of 2-Benzenesulphonylpiperidines and -pyrrolidines by Carbon  Nucleophiles: Synthesis of the Pyrrolidine Alkaloid Ruspolinone

Dearg S. Brown; Thomas Hansson; Steven V. Ley

doi:10.1055/s-1990-20983

Synlett 1990; 1990(1): 48-49
DOI: 10.1055/s-1990-20983

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Direct Substitution of 2-Benzenesulphonylpiperidines and -pyrrolidines by Carbon Nucleophiles: Synthesis of the Pyrrolidine Alkaloid Ruspolinone

Dearg S. Brown^* , Thomas Hansson, Steven V. Ley

^*Department of Chemistry, Imperial College of Science, Technology and Medicine, South Kensington, London SW7 2AY, England

Abstract

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Treatment of 2-benzenesulphonylpiperidines and -pyrrolidines with various carbon nucleophiles such as aryl, vinyl, and alkynyl organometallics (5 examples), or alternatively silyl enol ethers or allylsilanes in the presence of a Lewis acid (4 examples), afford the corresponding substitution products in good yield. The method has been used to prepare the pyrrolidine alkaloid natural product Ruspolinone (13).

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