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

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journal contribution
posted on 28.10.2005, 00:00 by Ross A. Miller, Randi M. Smith, Benjamin Marcune
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.