A Convenient Oxazole C-2 Protecting Group: The Synthesis of 4- and 5-Substituted Oxazoles via Metalation of 2-Triisopropylsilyloxazoles

Metalation of oxazoles at the 4 and 5 position was achieved after regioselective C-2 silyl protection. Removal of the protecting group was then accomplished under mild conditions allowing for a straightforward preparation of C-5 monosubstituted and C-4,5 disubstituted oxazoles. The first practical C...

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Veröffentlicht in:	Journal of organic chemistry 2005-10, Vol.70 (22), p.9074-9076
Hauptverfasser:	Miller, Ross A, Smith, Randi M, Marcune, Benjamin
Format:	Artikel
Sprache:	eng
Schlagworte:	Chemistry Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms Lithium - chemistry Molecular Structure Organic chemistry Oxazoles - chemical synthesis Oxazoles - chemistry Preparations and properties
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Beschreibung
Zusammenfassung:	Metalation of oxazoles at the 4 and 5 position was achieved after regioselective C-2 silyl protection. Removal of the protecting group was then accomplished under mild conditions allowing for a straightforward preparation of C-5 monosubstituted and C-4,5 disubstituted oxazoles. The first practical C-2 protecting group of oxazoles has been demonstrated.
ISSN:	0022-3263 1520-6904
DOI:	10.1021/jo051490m