Lewis Acid-Promoted Hetero Diels−Alder Cycloaddition of α-Acetoxynitroso Dienophiles

作者: Géraldine Calvet , Marion Dussaussois , Nicolas Blanchard , Cyrille Kouklovsky

DOI: 10.1021/OL0491336

关键词: StereochemistryChemistryDiels alderLewis acids and basesCycloadditionYield (chemistry)Cleavage (embryo)Nitroso

摘要: α-Acetoxynitroso compound 3 has been prepared as a new stable, isolable, and reactive dienophile in nitroso Diels−Alder reactions. The yield of the [4 + 2] cycloaddition α-acetoxynitroso with 1,3-dienes could be enhanced presence 20 mol % Lewis acid. An unexpected retro hetero-Michael reaction from 26 was observed, leading to cleavage N−O bond cycloadduct. This tandem Diels−Alder/retro sequence used cyclic acyclic 1,3-dienes.

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