The combination of N-arylimido sulfur ylides with enoldiazoacetates in the presence of a chiral catalyst form tetrasubstituted azetine-2-carboxylic acid derivatives by [3+1]-cycloaddition. Only copper(I) catalysis was effective for this transformation, and Cu(MeCN)4PF6 was the catalyst of choice in the formation of 2-azetines. Product yields were the highest in dichloromethane, and diphenylsulfur ylides gave higher product yields than their dimethyl or methylphenyl analogues. Reactions were performed at room temperature to avoid electroreversion of the azetine. [3+1]-Cycloaddition occurred with the triisopropylsilyl(TIPS)-protected enoldiazoacetate but not with the tert-butyldimethylsilyl(TBS)-protected enoldiazoacetate. This new cycloaddition methodology for azetines allows broad manipulation of substituents in high yields with excellent stereocontrol. Further research on azetine-2-carboxylic acid derivatives is still being conducted in our laboratory.

Utilizing a [3+1] cycloaddition methodology for asymmetric synthesis of azetines and researching subsequent reactions

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.