title: Asymmetric azidation-cycloaddition with open-chain peptide-based catalysts. A sequential enantioselective route to triazoles.
abstract: A family of beta-substituted histidine-containing peptides has been synthesized to probe the effect of noncovalent conformational rigidification on catalyst enantioselectivity. Unambiguous enhancement of enantioselectivity in the conjugate addition of azide to alpha,beta-unsaturated carboxylate derivatives has been achieved, enabling application to a sequential asymmetric azidation/cycloaddition for the synthesis of optically enriched triazoles and triazolines.
authors.affiliation: Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467-3860, USA.
authors.forename: David J
authors.initials: DJ
authors.lastname: Guerin
authors.forename: Scott J
authors.initials: SJ
authors.lastname: Miller
mesh_terms: D002384:Catalysis; D010455:Peptides / Q000737:chemistry*; D017433:Protein Structure, Secondary; D014230:Triazoles / Q000138:chemical synthesis*
chemical_list: D010455:Peptides; D014230:Triazoles