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- Title
Kinetic Resolution of a Planar–Chiral [2.2]Paracyclophane via Michael Addition to Nitroolefins Catalyzed by N‐Terminal Guanidinylated Helical Peptide.
- Authors
Tian, Jiaqi; Tamaribuchi, Kenya; Yoshikawa, Isao; Kudo, Kazuaki
- 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.
- Subjects
KINETIC resolution; PEPTIDES; PLANAR chirality; NITROALKENES; ESTERS
- Publication
European Journal of Organic Chemistry, 2024, Vol 27, Issue 16, p1
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.202400117