Organoboranes in organic synthesis. I. The reaction with α,α'-dibromo ketones in the presence of base

Abstract

α,α?-Dibromocycloalkanones react with organoboranes in the presence of base to give products dependent on the amount and type of base used. Small alkoxides yield mainly the reduced cycloalkanone; one equivalent of more hindered alkoxides also leads to reduction, but two equivalents of hindered alkoxides afford monoalkylcycloalkanones. Unsymmetrical dibromo ketones give alkylation exclusively on the least hindered side.