title: Asymmetric domino aza-Michael addition/[3 + 2] cycloaddition reactions as a versatile approach to α,β,γ-triamino acid derivatives.
abstract: Nonproteinogenic amino acids are prepared by an unprecedented domino aza-Michael addition-1,3-dipolar cycloaddition, leading to enantiopure highly substituted pyrrolidinopyrazolines. Nonaflyl azide serves as highly effective diazo transfer reagent, forming the link between the conjugate addition and cycloaddition steps. The resulting pyrrolidinopyrazolines can be rapidly transformed to either α,β,γ-triamino acids or 3,4-methano-β-prolines. Peptide coupling can be regioselectively conducted at each of the amino groups.
authors: Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic , Flemingovo nam. 2, 166 10, Prague 6, Czech Republic.
authors: Vojtěch
authors: V
authors: Kapras
authors: Radek
authors: R
authors: Pohl
authors: Ivana
authors: I
authors: Císařová
authors: Ullrich
authors: U
authors: Jahn
mesh_terms: D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D061565:Cycloaddition Reaction; D015394:Molecular Structure; D010455:Peptides / Q000737:chemistry*; D011392:Proline / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D011720:Pyrazoles / Q000737:chemistry; D011758:Pyrroles / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000596:Amino Acids; D010455:Peptides; D011720:Pyrazoles; D011758:Pyrroles; D011392:Proline; C072401:beta-proline