Efficient syntheses of new chiral peptidomimetic macrocycles through a configurationally driven preorganization

摘要

A new family of 32-membered ring peptidomimetic macrocycles has been efficiently obtained in a simple one-pot two-step reductive amination reaction,from easily prepared precursors.The structural and stereochemical variables have been explored in order to rationalize the obtained selectivity.The formation of the [2A+2B] tetraimine intermediate has been explained in terms of a very favorable configurationally driven preorganization as detected by NMR,CD and molecular modeling.