Chemistry of Sulfines, Part V: Chemo- and Stereoselective Synthesis and Hetero-Diels–Alder Reactions of Stable Sulfines

<div><p></p><p>The stereoselective synthesis of a variety of Z-sulfines by the oxidation of organic trithiocarbonates with m-chloroperbenzoic acid (m-CPBA) is described. Transient E-sulfines that are formed upon heating of Z-sulfines during cycloaddition reactions were trapped with 2,3-dimethyl-1,3-butadiene to yield only one of the possible diastereomers of the functionalized cyclic allylic sulfoxides. An X-ray analysis and ab initio calculations were performed to provide insight into the steric course of the oxidation and cycloaddition reactions.</p> <p>[Supplementary materials are available for this article. Go to the publisher's online edition of <i>Phosphorus, Sulfur, and Silicon and the Related Elements</i> for the following free supplemental files: Additional tables and figures.]</p>