Design of β-amino alcohols as chiral auxiliaries in the electrophilic amination of 1,3,2-oxazaphospholanes

Article abstract of DOI:10.1016/0040-4020(96)00839-3

Theoretical studies to predict the diastereoselectivity of the electrophilic amination of chiral 1,3,2-oxazaphospholanes led to the design of (1R), (2S)-1,3-diphenyl-2-(N-isopropylamino)-1-propanol 7 as a powerful chiral auxiliary. The experimental results are in good agreement with the calculations. An efficient synthesis of enantiomerically pure 7 is also reported.