For the first time, a 6p-electrocyclization of conjugated nitrodienes is being reported to yield a,�-unsaturated nitronates. The desired nitrodienes are found to be synthesized most efficiently through addition/elimination of vinyl zinc cuprates into �-thioethyl nitrocyclohexene, with vinyl cuprates readily prepared from the corresponding halide. Upon heating, the nitrodienes rearrange to form isolable nitronates, which are suitable substrates for dipolar cycloaddition with a variety of dipolarophiles to form tertiary nitrosoacetals. In addition, in the presence of various dipolarophiles, the conjugated nitrodienes are able to undergo tandem electrocyclization and dipolar cycloaddition to yield multicyclic nitrosoacetal products in a single pot.

Unprecedented 6π-electrocyclization of nitrodienes to yield nitronates

239th National Meeting (2010)

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