David A. Evans, Victor J. Cee, Thomas E. Smith, Keith J. Santiago
Selective Lithiation of 2-Methyloxazoles. Applications to Pivotal Bond Constructions in the Phorboxazole Nucleus.-Treatment of 2-methyloxazoles with BuLi or LiN(iPr) 2 results in selective formation of 5-lithiooxazoles or unselective reaction. In the presence of LiNEt 2 , a synthetically useful lithiation occurs which allows the selective generation of 2-(lithiomethyl)oxazoles. This approach appears to be general and can be applied to the synthesis of 2,4-disubstituted oxazole systems relevant to phorboxazole…
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