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Beilstein J. Org. Chem. 2025, 21, 1104–1115, doi:10.3762/bjoc.21.88
Graphical Abstract
Scheme 1: ᴅ-2-Aminoadipic acid (1) can be used to generate C6 aryl and alkynyl-modified pipecolic acid deriva...
Scheme 2: Methyl ester formation, followed by cyclization, N-formylation, as well as bromination under Vilsme...
Scheme 3: Suzuki–Miyaura cross-coupling reaction between bromide 2 and a variety of boronic acids 8.
Scheme 4: Reaction of 3a to (2R,6S)-9a and (2R,6R)-9a. The chromatograms prove the simple diastereoselection.
Figure 1: The minor diastereomer of the catalytic hydrogenation was assigned as (2R,6R)-9, based on the analy...
Figure 2: 1H NMR spectra with both signal sets for the chair and half-chair configuration as well as Newman p...
Figure 3: 1H NMR spectra with signal set for the chair configuration as well as Newman projection for both pr...
Scheme 5: a) Sonogashira–Hagihara cross-coupling reaction followed by b) NaBH3CN reduction of the N-acylimini...
Figure 4: 1H NMR with Newman projection for both protons H2 and H6 with corresponding dihedral angles ϕ for a...
Scheme 6: Overview of reduction and deprotection to the final pipecolic acid derivatives (2R,6S)-5.