Tandem Isomerization-Mannich Reactions from Allylic Alcohols and their Use for the Preparation of Four Diastereoisomers of 1-Amino-2-Methyl-1-Phenyloctan-3-ol

The tandem isomerization-Mannich reaction of octen-3-ol and benzylidene N-sulfonyl imine affords the corresponding beta-aminoketones in good yields. Diastereoselective reduction, followed by the deprotection of the primary amine, gives the expected 1-amino-2-methyl-1-phenyloctan-3-ol derivatives in excellent yields and in diastereomerically pure forms.