No abstract

No abstract

Allylic esters of TFA-protected amino acids undergo asymmetric Claisen rearrangements in the presence of cinchona alkaloids, giving rise to g,d-unsaturated amino acids in a highly stereoselective fashion. The products are useful precursors for the short and efficient synthesis of more complex compounds such as substituted 4-hydroxyornithines and iminosugars. Starting from the unsaturated amino acids, iodolactonization, bicylization and opening of the lactone ring with nucleophiles such as amino acids or peptides provide hydroxyproline derivatives directly incorporated into peptides.

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.