Enantiopure S-methylthiodinaphtho[2,1-c: 1′,2′-e][1,2]dithiinium hexachloroantimonate 3, transfers enantioselectively the MeS+ group to trans-hex-3-ene, leading to non-racemic thiiranium ion 4, which, in turn, reacts with MeCN–H2O allowing the synthesis of optically active double functionalised alkanes with enantiomeric excesses of up to 86%.
V. Lucchini, G. Modena and L. Pasquato, J. Chem. Soc., Chem. Commun., 1994, 1565 DOI: 10.1039/C39940001565
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