A novel acid-mediated nitro-Nazarov reaction of conjugated nitrodienes was employed to synthesize a variety of five-membered cyclic nitronates via a 4p electrocyclization. Also, tetracyclic nitronates were constructed through an interrupted nitro-Nazarov cyclization, which generated two new rings and an all carbon quaternary center. The corresponding cyclic nitronates were then subjected to a [3 + 2] dipolar cycloaddition to obtain highly functionalized nitroso acetals. It is known that these compounds can be reductively cleaved to construct complex amino alcohol derivatives. The utilization of both the nitro-Nazarov and the interrupted nitro-Nazarov reactions lead to the facile production of a variety of multicyclic ring systems, which we hope to show hold potential as useful intermediates in organic synthesis.

Acid-mediated nitro-Nazarov cyclization to generate cyclic nitronates

244th National Meeting (2012)

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