Application of a novel directing effect in an organocoppoer/orthoester reaction to the synthesis of deuterium labeled unsaturated esters

Article abstract of DOI:10.1016/S0040-4039(97)01599-2

Deuterium labeled methacrylates (5,6), tiglates (10,12), and senecioates (13,14,16,17), important for biosynthetic studies on the synthesis of carboxylic acids in carabid beetles, have been prepared using organocopper-alkyne coupling reactions. With 1,1,1,-triethoxypropyne as a coupling partner, a novel directing effect was observed; the 'branched' product was formed exclusively.