A convenient oxazole C-2 protecting group: the synthesis of 4-and 5-substituted oxazoles via metalation of 2-triisopropylsilyloxazoles

RA Miller, RM Smith, B Marcune

Index: Miller, Ross A.; Smith, Randi M.; Marcune, Benjamin Journal of Organic Chemistry, 2005 , vol. 70, # 22 p. 9074 - 9076

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Citation Number: 34

Abstract

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.