Cyclisation of aminyl radicals derived from amino acids

Article abstract of DOI:10.1016/S0040-4039(97)01413-5

α-Amino acid aminyl radicals have been generated from sulfenamide precursors using Bu₃SnH. The aminyl radicals undergo 5-exo-trig cyclisation reactions onto suitably placed N-alkenyl or α-alkenyl chains on the amino acids with reasonable diastereoselectivity. The α-ester of the amino acid imparts electrophilic behaviour to the aminyl radicals and facilitates cyclisation onto alkenes.