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. 2016 May 20;81(10):4081-97.
doi: 10.1021/acs.joc.6b00365. Epub 2016 Apr 29.

Sulfinyl-Mediated Stereoselective Overman Rearrangements and Diels-Alder Cycloadditions

Ignacio Colomer  1 , Chirag Gheewala  1 , Carmen Simal  1 , Marina Velado  1 , Roberto Fernández de la Pradilla  1 , Alma Viso  1
Affiliations

Sulfinyl-Mediated Stereoselective Overman Rearrangements and Diels-Alder Cycloadditions

Ignacio Colomer et al. J Org Chem. .

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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