Tetrahedron Letters

Acyl radical cyclisation onto pyrroles

SM Allin, WRS Barton, WR Bowman, T McInally

Index: Allin, Steven M.; Barton, William R.S.; Bowman; McInally, Tom Tetrahedron Letters, 2001 , vol. 42, # 44 p. 7887 - 7890

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Citation Number: 55

Abstract

Synthetically useful [1, 2-a]-fused pyrroles, eg 2, 3-dihydro-1H-pyrrolizidines substituted in the 1-and 7-positions, have been generated by acyl radical cyclisation onto pyrroles using N- (ω-acyl)-radicals generated from acyl-selenide precursors. The protocol does not require high pressures of CO. Mechanistic studies indicate the key role of azo radical initiators as oxidants of the intermediate π-radicals.