Abstract
4-Vinylazetidin-2-one (4) was converted into t-butyl (7aRS, 7bRS)-6,7,7a,7b-tetrahydro-3-methyl-6-oxo-1H-azeto[1,2-a]azirino[2,1-c]pyrazine-4-carboxylate (12; R = But)via thermolysis of the vinyl azide (9) in refluxing benzene. The configuration of the aziridine ring was assigned on the basis of nuclear Overhauser enhancement difference spectroscopy. t-Butyl was not an appropriate acid protecting group, but the corresponding diphenyl-t-butylsilyl ester (12; R = SiPh2But) was cleanly deprotected to give potassium (7aRS,7bRS)-6,7,7a,7b-tetrahydro-3-methyl-6-oxo-1 H-azeto[1,2,a]-azirino[2,1-c]pyrazine-4-carboxylate (12; R = K).
Published Version
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