The first chiral derivatives of 1-boraadamantane

Both (S)-(+)- [(S)-5] and (R)-(–)-2-methyl-1-boraadamantane [(R)-5] were isolated in 96% and 92% ee, respectively, by the crystallization of corresponding (S)-(–)- and (R)-(+)-phenylethylamine adducts from hexane and transformed into optically active 1-hydroxy-2-methyladamantanes by the carbonylation–oxidation sequence.