Kinetic Resolution of a Planar–Chiral [2.2]Paracyclophane via Michael Addition to Nitroolefins Catalyzed by N‐Terminal Guanidinylated Helical Peptide

N-terminal guanidinylated resin–supported helical peptides were found to catalyze the kinetic resolution of a planarly chiral 4-(2-nitrovinyl)[2.2] paracyclophane via asymmetric Michael addition with an s-factor reaching up to 111.

Abstract

Kinetic resolution of 4-(2-nitrovinyl)[2.2]paracyclophane based on N-terminal–guanidinylated resin–bound helical peptide catalyzed asymmetric Michael addition of malonate esters was developed. This approach provides a new pathway to enantiopure paracyclophane derivatives characterized by both planar and central chirality, along with the recovery of the chiral substrate with a selectivity factor of up to 111. Additionally, the synthetic potential of the resulting products has been showcased through their successful transformation into derivatives of β-substituted γ-aminobutyric acid.

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