N-Allylamides and allyl esters of bisalkoxycarbonylaminoacetic acid (5) were found to cyclize in strong acid solutions to the five-membered pyrrolidones (6; Y = NH) and butyrolactones (6; Y = O) rather than to the corresponding six-membered piperidinones (8; Y = NH) or the six-membered lactones (8, Y = O).
D. Ben-Ishai, J. Chem. Soc., Chem. Commun., 1980, 687 DOI: 10.1039/C39800000687
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