Sulfinyl-Mediated Stereoselective Overman Rearrangements and Diels-Alder Cycloadditions.
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.
Instituto de Química Orgánica General, IQOG-CSIC , Juan de la Cierva 3, 28006 Madrid, Spain.
Ignacio
I
Colomer
Instituto de Química Orgánica General, IQOG-CSIC , Juan de la Cierva 3, 28006 Madrid, Spain.
Chirag
C
Gheewala
Instituto de Química Orgánica General, IQOG-CSIC , Juan de la Cierva 3, 28006 Madrid, Spain.
Carmen
C
Simal
Instituto de Química Orgánica General, IQOG-CSIC , Juan de la Cierva 3, 28006 Madrid, Spain.
Marina
M
Velado
Instituto de Química Orgánica General, IQOG-CSIC , Juan de la Cierva 3, 28006 Madrid, Spain.
Roberto
R
Fernández de la Pradilla
Instituto de Química Orgánica General, IQOG-CSIC , Juan de la Cierva 3, 28006 Madrid, Spain.
Alma
A
Viso