Radical cyclisation of amino aldehydes leading to hydroxy pyrrolidines and piperidines

Article abstract of DOI:10.1016/S0040-4039(97)01316-6

The cyclisation of amino aldehydes using Bu₃SnH in boiling benzene is reported. The reaction proceeds via addition of a tributyltin radical to the aldehyde forming an O-stannyl ketyl and radical cyclisation onto electron poor or rich double bonds gives rise to hydroxy pyrrolidines and piperidines.