Sulfinyl-Mediated Stereoselective Overman Rearrangements and Diels-Alder Cycloadditions
Ignacio Colomer1, Chirag Gheewala1, Carmen Simal1
1Instituto de Química Orgánica General, IQOG-CSIC , Juan de la Cierva 3, 28006 Madrid, Spain.
Abstract:
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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