title: Lewis acid-promoted hetero Diels-Alder cycloaddition of alpha-acetoxynitroso dienophiles.
abstract: [reaction: see text] alpha-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 of alpha-acetoxynitroso dienophile with 1,3-dienes could be enhanced in the presence of 20 mol % Lewis acid. An unexpected retro hetero-Michael reaction from 26 was observed, leading to the cleavage of the N-O bond of the cycloadduct. This tandem nitroso Diels-Alder/retro hetero-Michael sequence has been used with cyclic and acyclic 1,3-dienes.
authors.affiliation: Laboratoire de Synthèse des Substances Naturelles, Institut de Chimie Moléculaire et des Matériaux d'Orsay, Batiment 410, Université Paris Sud, 91400 Orsay-France.
authors.forename: Géraldine
authors.initials: G
authors.lastname: Calvet
authors.forename: Marion
authors.initials: M
authors.lastname: Dussaussois
authors.forename: Nicolas
authors.initials: N
authors.lastname: Blanchard
authors.forename: Cyrille
authors.initials: C
authors.lastname: Kouklovsky