F. Almqvist et T. Frejd, NEIGHBORING GROUP PARTICIPATION IN A REGIOSELECTIVE AND STEREOSELECTIVE CHLORINATION OF A BICYCLO[2.2.2]OCTANONE, Journal of organic chemistry, 61(20), 1996, pp. 6947-6951
The zinc chloride-mediated acetylation of the optically active silyl e
nol ether 2a gave the beta-diketone 3a (48%) together with the regio-
and stereoselectively chlorinated compound 4 (27%). The yield of 4 inc
reased to 70% by starting from the O-acetyl derivative 2c. The chlorin
ation most likely occurs via neighboring group participation by the en
do acetoxy group.