234075-91-3Relevant academic research and scientific papers
Selective lithiation of 2-methyloxazoles. Applications to pivotal bond constructions in the phorboxazole nucleus
Evans, David A.,Cee, Victor J.,Smith, Thomas E.,Santiago, Keith J.
, p. 87 - 90 (1999)
(equation presented) R = Alkyl, Vinyl, Aryl 6:7 >95:5 The lithiation of 2-methyloxazoles with alkyllithium and hindered lithium amide bases generally results in the competitive formation of a mixture of 5-lithio-and 2-(lithiomethyl)oxazole isomers. Herein a synthetically useful lithiation method which allows for the selective formation of 2-(lithiomethyl)oxazole is described. Diethylamine has been found to be a kinetically competent proton source that will mediate the equilibration of the kinetically formed 5-lithiooxazole to its more stable 2-(lithiomethyl)oxazole counterpart. Application of this metalation strategy with lithium diethylamide to two important bond constructions relevant to a projected phorboxazole synthesis is presented.
