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Paper | Special issue | Vol 99, No. 1, 2019, pp.446-464
Published online, 24th October, 2018
DOI: 10.3987/COM-18-S(F)41
Heterospirocyclic 3-Amino-2H-azirines as Convenient Building Blocks in Peptide Synthesis

Christoph Strässler and Heinz Heimgartner*

*Department of Chemistry, University of Zürich, Winterthurerstrasse 190, CH-8057 Zürich, Switzerland

Abstract

Heterospirocyclic 3-amino-2H-azirines with a tetrahydropyran (Thp), tetrahydrothiopyran (Tht), or N-protected piperidine (Pip) moiety are useful reagents for the preparation of peptides containing the corresponding six-membered heterocyclic 4-amino-4-carboxylic acid unit. In the present study, tripeptides of the type H-Asp-D-Ala-Xaa-OMe, where Xaa is the heterocyclic amino acid, were prepared according to the ‘azirine/oxazolone method’.