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1 article(s) from Bieliauskas, Aurimas

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

Jolita Bruzgulienė,
Greta Račkauskienė,
Aurimas Bieliauskas,
Vaida Milišiūnaitė,
Miglė Dagilienė,
Gita Matulevičiūtė,
Vytas Martynaitis,
Sonata Krikštolaitytė,
Frank A. Sløk and
Algirdas Šačkus

Beilstein J. Org. Chem. 2022, 18, 102–109, doi:10.3762/bjoc.18.11

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Graphical Abstract

Figure 1: Examples of amino-functionalized 1,2-oxazole derivatives I–VIII.

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Scheme 1: Conversion of cyclic amino acids to 1,2-oxazole derivatives.

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Scheme 2: Plausible mechanisms for the formation of 1,2-oxazoles 4a–h and VII from β-enamino ketoesters 3a–h ...

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Figure 2: (a) ¹H NMR (italics), ¹³C NMR (normal), and ¹⁵N NMR (bold) chemical shifts (ppm) of compound 3a in ...

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Scheme 3: Synthesis of compound ¹⁵N-1,2-oxazole 5. The coupling constants of J_HN and J_CN from ¹⁵N2 are indica...

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Figure 3: Stacked chromatogram view of pairs of enantiomers with area, %: (R)-4b, ee 100% (t_R = 10.1 min) and...

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Figure 4: (a) Structure of 4b with syn- and anti-conformers; (b) superimposed ¹H NMR and 1D gradient NOE spec...

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Scheme 4: Synthesis of 2-[4-(methoxycarbonyl)-1,2-oxazol-5-yl]cycloaminyl-1-ium trifluoroacetates 6a,b.

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Figure 5: ORTEP diagram of the asymmetric unit consisting of two cations 6b(A) and 6b(B) and triflate anions.

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Published 12 Jan 2022

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