Abstract: The stereochemistry of the carbon-carbon bond-forming step in the electrophilic intermolecular 1'-2 condensation of 3-methyl-2-butenyl acetate (I-OAc) to yield lavandulyl acetate (2-OAc) was studied. Treatment of (lS)-[1-2H] 3-methyl-2-butenyl acetate ((lS)-[l-'H] 1- OAc) with aluminum trichloride in ethyl acetate gave labeled lavandulyl acetate ([1, 3-'H2] 2- OAc)(30%) and isoprene (65%) as the major products. The configurations at C (1), C (2), ...
