[GRAPHICS] The synthesis, reactivity, and stereochemical behavior of differently substituted iodoalkenyl alpha,beta-unsaturated sulfoxides in intramolecular Heck reaction is described. Particularly, the 2-(N,N dimethylamino)phenylsulfinyl group is demonstrated to be an effective chiral auxiliary for the intramolecular Heck reaction of 2-iodo-1,6-(or 1,7)dienes. A desulfinylation sequence removes the auxiliary and yields cyclic compounds of high enantiopurity.
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