Face selection in the reduction of p,p'-disubstituted 5,7-diphenyl-2- adamantanones and hydrolysis of the corresponding 2-adamantyl tosylates

Article abstract of DOI:10.1021/jo00080a012

The reduction of 5,7-diphenyl-2-adamantanone with sodium borohydride in 2- propanol is affected by the introduction of a p-nitro substituent in one of the rings: the E-alcohol is obtained in small but easily measurable excess of 1.30:1. Conversely, the in