Novel chiral dithioethers derived from L-tartaric acid

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 (approximate to 50%). The analogous ditriflate 4 with benzyl ether protecting groups, having a skeleton without restricted rotation, gave the thiolane 9 as the main product. (C) 2002 Elsevier Science Ltd. All rights reserved.