Synthesis, resolution, and applications of 3-amino-2,2-dimethyl-1,3-diphenylpropan-1-ol, a conformationally restricted 1,3-aminoalcohol

Efficient synthetic routes to both syn and anti diastereomers of a conformationally restricted 1,3-aminoalcohol were devised. Resolution of the aminoalcohols was accomplished through diastereomeric salt with R-(−)-O-acetyl mandelic acid. These aminoalcohols were examined as ligands for two standard reactions, namely, enantioselective addition of Et2Zn to aldehydes and reduction of prochiral ketones with BH3.