Journal of Organic Chemistry p. 4081 - 4087 (2016)
Update date:2022-08-15
Topics:
Colomer, Ignacio
Gheewala, Chirag
Simal, Carmen
Velado, Marina
Fernández De La Pradilla, Roberto
Viso, Alma
Sulfinyl trichloroacetamides are readily obtained in excellent yields through a highly stereoselective Overman rearrangement. Related bis-allylic substrates lead to amido 2-sulfinyl butadiene derivatives in excellent yields, with total chemo- and diastereoselectivity. These amido dienyl sulfoxides undergo highly selective Diels-Alder cycloadditions with N-phenylmaleimide with remarkable stereocontrol by the sulfoxide moiety.
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