Preparative scale synthesis of functionalized bioxazole

Preparative scale synthesis of functionalized bioxazole

Seven-step preparative scale synthesis of chiral, enantiomerically pure 2'-aminomethyl-2,4'-bioxazole has been accomplished from L- tert -Leu. The 2,4'-bioxazole subunit can be functionalized at position C-5' by a regioselective lithiation, followed by the reaction with a suitabl...

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Veröffentlicht in:Chemistry of heterocyclic compounds (New York, N.Y. 1965) N.Y. 1965), 2020-03, Vol.56 (3), p.355-364
Hauptverfasser: Kazak, Mihail, Vasilevska, Anna, Suna, Edgars
Format: Artikel
Sprache:eng
Schlagworte:
Chemistry
Chemistry and Materials Science
Cross coupling
Lithium
Organic Chemistry
Pharmacy
Synthesis
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Zusammenfassung:Seven-step preparative scale synthesis of chiral, enantiomerically pure 2'-aminomethyl-2,4'-bioxazole has been accomplished from L- tert -Leu. The 2,4'-bioxazole subunit can be functionalized at position C-5' by a regioselective lithiation, followed by the reaction with a suitable electrophile. The C-5'-lithium intermediate can be also transmetalated into organozinc species and used in Pd-catalyzed Negishi cross coupling.
ISSN:0009-3122
1573-8353
DOI:10.1007/s10593-020-02667-8