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Ethyl 1,3-dithiane-2-carboxylate is used in syn-selective aldol reactions. It undergoes asymmetric oxidation to give trans bis-sulfoxide. It is used to generate carbanon, which finds application in the preparation of alfa- keto esters.
Alkylation of the anion provides a route to ɑ-keto acids (by dethioketalization with NBS), or to substituted acetic acids (by desulfurization): J. Org. Chem., 37, 505 (1972). For phase-transfer alkylation using allylic bromides, see: Liebigs Ann. Chem., 1589 (1982). With crotyl bromide, approx. 95% allylic rearrangement occurs.
The lithiated derivative undergoes 1,4- (Michael) addition to a variety of ɑß-unsaturated compounds. However, the Mg derivative prepared by metallation with an alkylmagnesium halide gives an allylic alcohol by 1,2-addition: Chem. Ber., 114, 2924 (1981).
Pathak, R. B.; Dobson, B. C.; Ghosh, N.; Ageel, K. A.; Alshawish, M. R.; Saruengkhanphasit, R.; Coldham, I. Synthesis of the tricyclic core of manzamine A. Org. Biomol. Chem. 2015, 13 (11), 3331-3340.
Gaggero, N.; Albanese, D. C. M.; Nava, D. A new approach to 4,6-disubstituted-3,4-dihydropyran-2-ones by Domino Michael addition-cyclization reaction under PTC conditions. Tetrahedron 2014, 70 (45), 8744-8749.
Gefahrenhinweise (EU): H226
Flammable liquid and vapour.
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