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Directed Metalation of Heterocycles, 5-Methoxy-2-phenyloxazol-4-yllithium: An Approach to α,β-Dehydroamino Acids
2010
Organic Chemistry International
Preserved Fulltext
5-Methoxy-2-phenyloxazole was deprotonated at C4 (by n-BuLi or LDA, in THF at −78C∘). The resulting anion was generally unreactive to alkylation (except methylation with MeI-TMEDA) but added to PhCHO and Me2CHCHO. The alcohols thus produced dehydrated and ring opened in acid, to the corresponding α,β-dehydroamino acids in moderate overall yields.
doi:10.1155/2010/452956
fatcat:g4thmv25izgrtco7cvmb555mea