237. Regiodivergent Synthesis of Oxadiazocines via Dirhodium-Catalyzed Reactivity of Oxazolidines and α-Imino Carbenes
     Olivier Viudes, Alejandro Guarnieri-Ibáñez, Céline Besnard, Jerome Lacour
     Synlett 2023, 34, 1472-1476

Using electron-rich or electron-poor N-substituted oxazolidines as substrates, selective formation of either ammonium or oxonium ylides is possible in the presence of α-imino carbenes. As such, treatment of 5-membered oxazolidine precursors with N-sulfonyl-1,2,3-triazoles under dirhodium catalysis (2 mol%) affords the regiodivergent synthesis of either 8-membered 1,3,6- or 1,4,6-oxadiazocines upon the initial N- or O-reactivity with the carbene.

DOI : 10.1055/a-2072-4537 

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