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Published on: August 12, 2019
Asymmetric domino aza-Michael addition/[3 + 2] cycloaddition reactions as a versatile approach to α,β,γ-triamino acid
Vojtěch Kapras1, Radek Pohl, Ivana Císařová
1Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic , Flemingovo nam. 2, 166 10, Prague 6, Czech Republic.
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.
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