作者: Géraldine Calvet , Marion Dussaussois , Nicolas Blanchard , Cyrille Kouklovsky
DOI: 10.1021/OL0491336
关键词: Stereochemistry 、 Chemistry 、 Diels alder 、 Lewis acids and bases 、 Cycloaddition 、 Yield (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.