The reduction of N-protected amino ketones can be carried stereoselectively to produce either thesyn- or anti-amino alcohol diastereomer. Carbamate-protected amino ketones can be reducedpredictably and selectively to anti-amino alcohols with LiAlH(O-t-Bu)3 in ethanol at −78 °C. N-Trityl-protected amino ketones can be reduced selectively to syn-amino alcohols with LiAlH(O-t-Bu)3 inTHF at −5 °C.