Concise pathway to new multifunctionalized constrained pentacin derivatives by means of two stereospecific tandem reactions

Article abstract of DOI:10.1002/ejoc.201100593

Starting from Boc-activated diketopiperazines, original bicyclic derivatives of trans-and cis-2-aminocyclopentane carboxylic acid were prepared by using two stereospecific tandem reactions. One of them is a tandem transannular rearrangement of activated lactams/alkylation process leading to the stereoselective synthesis of suitably chiral pyrrolidine-2, 4-diones, allowing subsequent Michael-initiated ring closure, a simple and concise route to original multifunctionalized alicyclic ss-amino esters.