Regioselective synthesis of methyl 5-(N-Boc-cycloaminyl)-1,2-oxazole-4-carboxylates as new amino acid-like building blocks

Autor: Jolita Bruzgulienė, Greta Račkauskienė, Aurimas Bieliauskas, Vaida Milišiūnaitė, Miglė Dagilienė, Gita Matulevičiūtė, Vytas Martynaitis, Sonata Krikštolaitytė, Frank A. Sløk, Algirdas Šačkus
Jazyk: angličtina
Rok vydání: 2022
Předmět:
Zdroj: Beilstein Journal of Organic Chemistry, Vol 18, Iss 1, Pp 102-109 (2022)
Druh dokumentu: article
ISSN: 1860-5397
DOI: 10.3762/bjoc.18.11
Popis: A convenient and efficient synthesis of novel achiral and chiral heterocyclic amino acid-like building blocks was developed. Regioisomeric methyl 5-(N-Boc-cycloaminyl)-1,2-oxazole-4-carboxylates were prepared by the reaction of β-enamino ketoesters (including azetidine, pyrrolidine or piperidine enamines) with hydroxylamine hydrochloride. Unambiguous structural assignments were based on chiral HPLC analysis, 1H, 13C, and 15N NMR spectroscopy, HRMS, and single-crystal X-ray diffraction data.
Databáze: Directory of Open Access Journals