Azomethine ylide cycloaddition reactions are some of the most powerful and well-studied chemical transformations to construct (hetero)cyclic frameworks. On the other hand, the cycloadditions of azomethine ylides bearing <i>N</i>-alkoxy substituents has largely been overlooked. This has been the case despite the potential for accessing heterocycles with a useful cleavable tether which can be manipulated downstream (via N-O bond cleavage). Herein, we describe our efforts in the pursuit of intramolecular <i>N</i>-alkoxyazomethine ylide generation from oximes with a diazoketone moiety tethered to the oxygen atom and the disparate reactivities observed. The research plan discussed will probe three key questions: (1) Does the desired [3+2] cycloaddition take place in the presence of a catalyst and dipolarophile? (2) What is the effect of having a diazo ketone vs an a-diazo-b-ketoester moiety tethered to the oxime oxygen? (3) How does the transition-state ring size effect the intramolecular ylide formation and stability?

Efforts towards Rh(II)-catalyzed N-alkoxyazomethine ylide generation

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.