Neighboring Group Participation in a Regio- and Stereoselective Chlorination of a Bicyclo[2.2.2]octanone.
The zinc chloride-mediated acetylation of the optically active silyl enol ether 2a gave the beta-diketone 3a (48%) together with the regio- and stereoselectively chlorinated compound 4 (27%). The yield of 4 increased to 70% by starting from the O-acetyl derivative 2c. The chlorination most likely occurs via neighboring group participation by the endo acetoxy group.
Almqvist
Fredrik
F
Organic Chemistry 1, Department of Chemistry, Lund University, P. O. Box 124, S-221 00 Lund, Sweden.
Frejd
Torbjörn
T