Asymmetric Diels-Alder reactions of a new enantiomerically pure sulfinylquinone: a straightforward access to functionalized Wieland-Miescher ketone analogues with (R) absolute configuration.

An efficient and highly stereocontrolled preparation, on a large scale, of two new Wieland-Miescher-type diketones is described. The approach centers on a diastereoselective Diels-Alder reaction using a new enantiomerically pure sulfinylquinone. Mechanistic investigations of this cycloaddition on several dienes are described.