Ring-Opening Regio-, Diastereo-, and Enantioselective 1,3-Chlorochalcogenation of Cyclopropyl Carbaldehydes.

meso-Cyclopropyl carbaldehydes are treated in the presence of an organocatalyst with sulfenyl and selenyl chlorides to afford 1,3-chlorochalcogenated products. The transformation is achieved by a merged iminium-enamine activation. The enantioselective desymmetrization reaction, leading to three adjacent stereocenters, furnished the target products in complete regioselectivity and moderate to high diastereo- and enantioselectivities (d.r. up to 15:1 and e.r. up to 93:7).