233591-88-3Relevant academic research and scientific papers
Application of the peptide Claisen rearrangement toward the synthesis of cyclic peptides
Kazmaier, Uli,Maier, Sabine
, p. 1763 - 1766 (1999)
(formula presented) Allylic esters of peptides undergo Claisen rearrangement after deprotonation in the presence of tin chloride, giving rise to allylated peptides. Subsequent N-allylation and ring-closing metathesis provides the corresponding cyclic pept
A straightforward approach towards cyclic peptides via ring-closing metathesis - Scope and limitations
Kazmaier, Uli,Hebach, Christina,Watzke, Anja,Maier, Sabine,Mues, Heike,Huch, Volker
, p. 136 - 145 (2007/10/03)
N- and C-terminal diallylated peptides are obtained by several approaches, such as peptide Claisen rearrangement, N- and O- allylation, and the Ugi reaction of allyl-protected components. These diallylated peptides are suitable substrates for ring-closing metathesis and the success of this cyclisation was investigated with respect to the ring size, the position of the allyl moieties and the reaction parameters. In general, excellent yields are obtained for cyclisation of allyl glycine subunits and N-allylated amides, while allyl esters and allyl carbamates often presented serious problems. However, yields of up to 73% were obtained under optimised conditions, and the new generated double bond is formed with excellent trans-selectivity.
