Novel chiral dithioethers derived from l-tartaric acid |
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Institution: | 1. N.D. Zelinsky Institute of Organic Chemistry, Moscow, Russian Federation;2. Library for Natural Sciences, Moscow, Russian Federation |
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Abstract: | The synthesis of a new family of systematically modified chiral dithioethers to be used as ligands is described. Phenylthioether derivative 5 and fluorine-containing dithioether ligands 6–8 and 13–15 were prepared by direct reaction of phenylthiol and o-, m- or p-fluorophenylthiol with two different ditriflate derivatives based on the l-tartaric skeleton. The chiral ditriflate 12 containing a dioxolane moiety was reacted with ethane- and propanedithiol, producing cyclic dithioethers 16 and 17, respectively, in good yields (≈50%). The analogous ditriflate 4 with benzyl ether protecting groups, having a skeleton without restricted rotation, gave the thiolane 9 as the main product. |
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