γ-Lactams and furan bispyrrolidines via iodine mediated cyclisation of homoallylamines

Abstract

1,3,5-Substituted pyrrolidin-2-ones were synthesised via an iodine mediated cyclisation of 3-methyl substituted homoallylamines in good to excellent yield, as mixtures of diastereoisomers. Furan bispyrrolidines were formed as single diastereoisomers when 3-phenyl homoallylamines were employed in an analogous reaction.

Abstract

1,3,5-Substituted pyrrolidin-2-ones were synthesised via an iodine mediated cyclisation of 3-methyl substituted homoallylamines in good to excellent yield, as mixtures of diastereoisomers. These were separable and their identity confirmed by techniques including single crystal X-ray diffraction. When 3-phenyl substituted homoallylamines were cyclised intriguing fused tricyclic motifs were obtained as C ₂-symmetric racemates, whose structures were also confirmed by techniques including single crystal X-ray diffraction analysis.