Abstract
A regioselective magnesiation of the 2-pyrone scaffold was developed. Magnesiation of this heterocycle by using TMPMgCl center dot LiCl (TMP = 2,2,6,6-tetramethylpiperidyl) followed by trapping reactions with electrophiles such as aldehydes, allylic bromides, acid chlorides, and aryl iodides provided functionalized 2-pyrones. Furthermore, methyl coumalate and 3,5-dibromo-2H-pyran-2-one were zincated by using TMPZnCl center dot LiCl to afford zincated heterocycles, which reacted with typical electrophiles. A second magnesiation at position C3 of the 2-pyrone scaffold was achieved by using TMPMgCl center dot LiCl. Also, the zincation of the 4-pyrone scaffold at position C2 is reported, leading to functionalized 4-pyrones.
Dokumententyp: | Zeitschriftenartikel |
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Fakultät: | Chemie und Pharmazie > Department Chemie |
Themengebiete: | 500 Naturwissenschaften und Mathematik > 540 Chemie |
ISSN: | 0039-7881 |
Sprache: | Englisch |
Dokumenten ID: | 67383 |
Datum der Veröffentlichung auf Open Access LMU: | 19. Jul. 2019, 12:22 |
Letzte Änderungen: | 04. Nov. 2020, 13:49 |