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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Silver(i)-mediated oxazoline formation: a mild route to 2,4-oxazoles in peptides
Adam S Pickett1, Jacob W Campbell1, Katherine M Cox1
1Department of Chemistry, Dalhousie University 6243 Alumni Crescent Halifax NS B3H 4R2 Canada carlie.charron@dal.ca.
Abstract:
We present a silver-promoted cyclization of peptide thioamides that enables site-specific insertion of oxazole and methyloxazole motifs through oxazoline intermediates. Demonstrated in di- and tetrapeptides, this mild, moisture-tolerant methodology delivers high-yield products, offering a robust and general strategy for constructing structurally diverse, conformationally constrained oxazole-containing peptidomimetics.
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