Tandem 6π-Electrocyclization and Cycloaddition of Nitrodienes to Yield Multicyclic Nitroso Acetals
作者： Gardner S. Creech , Ohyun Kwon
DOI: 10.1021/JA1038819
关键词:
摘要: Upon heating, nitrodienes rearrange through 6pi-electrocyclization to form nitronate intermediates, which can be captured tandem [3 + 2] dipolar cycloadditions highly functionalized nitroso acetals. The one-pot, two-step domino process is efficient, proceeding with good facial selectivity and exoselectivity. Dipolarophiles featuring electron-rich, -neutral, -deficient carbon-carbon double bonds are viable substrates for the in situ generated nitronates. In addition, acetal products hydrogenolyzed selectively densely spirocyclic hydroxy amides or gamma-amino acids.
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