Synthesis of Enantiomerically Pure 2-Heteroaromatic-Substituted 1,2-Amino Alcohols from Chiral tert-Butanesulfinyl Aldimines

Nine R / S pairs of 2-heteroaromatic-substituted 1,2-amino alcohols were synthesized through 1,2-nucleophilic addition between chiral N -( tert -butylsulfinyl)imines and heteroaromatic carbanions. In most cases, the R S -isomer of N -( tert -butylsulfinyl)imines afforded the R amino alcohol from deprotection of the major diastereomer, and S S -imines afforded the S product. In general, this procedure allows for the preparation of a variety of enantiomeric pairs of 2-heteroaromatic-substituted 1,2-amino alcohols on a practical scale (>10 g) in two steps in good yields.