Optically active 2H-azepines: Synthesis and rearrangement into their 3H-isomers

Article abstract of DOI:10.1016/0040-4020(96)00629-1

A general synthesis of optically active 2H-azepines 12 starting from α-amino acids is described. The 2H-azepines easily rearrange into the corresponding 3H-isomers 18. The pungent taste of chalciporone (1) and simple 2,7-dialkylsubstituted 2H-azepines is due to the 2H-azepine nucleus and is independent of the absolute configuration at C-2.