Journal
ORGANIC LETTERS
Volume 22, Issue 15, Pages 6197-6202Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.0c02331
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A new non-natural beta-amino acid, named 3-Ar-beta-Morph, was designed and synthesized via a regio- and diastereoselective Pd-catalyzed C(sp(3))H-arylation of the corresponding 2S,6S-(6-methoxymorpholin-2-yl)carboxylic acid, readily available from glucose. According to the computational prevision and confirmed by IR and NMR data, the insertion of 3-Ar-beta-Morph in a model foldamer represents a way to stabilize a PPII-like helix through the presence of two gamma-turns, secondary structure motifs induced by the morpholine ring, and the trans-tertiary amide bond.
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