Tetrahedron

Substitution reactions of 2-benzenesulphonyl cyclic ethers with carbon nucleophiles

DS Brown, M Bruno, RJ Davenport, SV Ley

Index: Brown, Dearg S.; Bruno, Maurizio; Davenport, Raymond J.; Ley, Steven V. Tetrahedron, 1989 , vol. 45, # 13 p. 4293 - 4308

Full Text: HTML

Citation Number: 115

Abstract

Direct substitution of 2-benzenesulphonyl cyclic ethers was studied using a variety of carbon nucleophiles. These nucleophiles included organozinc reagents (derived from aryl, vinyl and alkynyl Grignard reagents) or silyl enol ethers, silyl ketene acetals, allylsilanes and trimethylsilylcyanide in the presence of aluminum chloride. A general selectivity for the formation of the trans-product was observed using 6-subsitituted sulphones.