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

Autor:	Bruzgulienė, Jolita, Račkauskienė, Greta, Bieliauskas, Aurimas, Milišiūnaitė, Vaida, Dagilienė, Miglė, Matulevičiūtė, Gita, Martynaitis, Vytas, Krikštolaitytė, Sonata, Slok, Frank A., Šačkus, Algirdas
Přispěvatelé:	Beilstein-Institut
Rok vydání:	2022
Předmět:	15N) C-13 Science 15N-labeled 1 2-oxazole NMR (1H Organic Chemistry NMR (H-1 Full Research Paper β-enamino ketoesters X-ray structure analysis Chemistry QD241-441 N-15) 1 2-oxazole (isoxazole) heterocyclic amino acids 13C beta-enamino ketoesters N-15-labeled 1 2-oxazole
Zdroj:	Beilstein Journal of Organic Chemistry Beilstein Journal of Organic Chemistry, Vol 18, Iss 1, Pp 102-109 (2022)
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:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::1ff311b7d483a510a4da7f7576808831 https://doi.org/10.3762/bjoc.18.11 Zobrazit plný text záznamu