Stereoselective transformation of amines to alcohols enriched with the enantiomer formed by respectively inversion and retention of configuration

Article abstract of DOI:10.1016/S0957-4166(97)00240-1

We hereby report the transformation of the chiral amines 1-3 to the corresponding alcohols 4-6 with 90-100% inversion of stereochemistry. KNO₂ and catalytic amounts of 18-crown-6 were used in the nucleophilic attack on the N,N-ditosylimide intermediates 1a-3a. A diazotization reaction for the corresponding preparation of the alcohols 4-6 from the respective amines 1-3 with 65-90% retention of configuration is also discussed.