Ring Closing Metathesis of Unsaturated Amides as a Route to Short and Medium-Sized Unsaturated Lactams and to Ethylenic Pseudopeptides
31 December 2001 (online)
Five- to eight-membered unsaturated lactams have been obtained through ring-closing metathesis of unsaturated amides of various chain lengths and substitution patterns. The obtention of nine-membered unsaturated lactams by the same procedure met only with limited success. Also described in this Letter is the obtention of the Z-ethylenic pseudopeptidic analog of l-Phe-l-Phe through hydrolytic ring opening of (3R,6S)-3,6-dibenzyl-3,6-dihydro-2-pyridone obtained by RCM.
amides - lactams - metathesis - peptides - ring closure