| Title |
Regioselective synthesis of methyl 5-(N-Boc-cycloaminyl)-1,2-oxazole-4-carboxylates as new amino acid-like building blocks / |
| Authors |
Bruzgulienė, Jolita ; Račkauskienė, Greta ; Bieliauskas, Aurimas ; Milišiūnaitė, Vaida ; Dagilienė, Miglė ; Matulevičiūtė, Gita ; Martynaitis, Vytas ; Krikštolaitytė, Sonata ; Slok, Frank A ; Šačkus, Algirdas |
| DOI |
10.3762/bjoc.18.11 |
| Full Text |
|
| Is Part of |
Beilstein journal of organic chemistry.. Frankfurt am Main : Beilstein-Institut. 2022, vol. 18, p. 102-109.. ISSN 1860-5397 |
| Keywords [eng] |
beta-enamino ketoesters ; heterocyclic amino acids ; N-15-labeled 1,2-oxazole ; NMR (H-1 ; C-13 ; N-15) ; 1,2-oxazole (isoxazole) ; X-ray structure analysis |
| Abstract [eng] |
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 beta-enamino ketoesters (including azetidine, pyrrolidine or piperidine enamines) with hydroxylamine hydrochloride. Unambiguous structural assignments were based on chiral HPLC analysis, H-1, C-13, and N-15 NMR spectroscopy, HRMS, and single-crystal X-ray diffraction data. |
| Published |
Frankfurt am Main : Beilstein-Institut |
| Type |
Journal article |
| Language |
English |
| Publication date |
2022 |
| CC license |
|
