ChemInform Abstract: Neighboring Group Participation in a Regio‐ and Stereoselective Chlorination of a Bicyclo(2.2.2)octanone.

Abstract

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 (I) gives the β-diketone (III) together with the regio-and stereoselectively chlorinated compound (IV). The chlorination most likely occurs via neighboring group participation by the endo acetoxy group. -(ALMQVIST, F.; FREJD, T.; J.