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An efficient, three-step synthesis of N-vinyl-2-azetidinones 7 starting from α- or β-amino ester imines 3 has been developed. Staudinger reaction between imines 3 and a ketene precursor gave 2-azetidinones 4. Enolate formation on the amino ester moiety of the 2-azetidinone 4, selenation, and finally m-CPBA treatment, afforded N-vinyl-2-azetidinones 7 in fair to excellent yields, with total retention of the stereochemistry of the starting material. Two examples of the use of compounds 7 in preparing bi- and tricyclic 2-azetidinones are presented.
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Alcaide et al. (1998) studied this question.
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