Stereocontrolled Synthesis of 1,3-Amino Alcohols by Reduction of Substituted 2-{1-[(tert-Butylsulfinyl)amino]alkyl}cyclohexanones

Assembly of diethylzinc, cyclohex-2-en-1-one, and a chiral N-tert-butylsulfinyl imine in the presence of an appropriate phosphoramidite ligand yields a beta-sulfinylamino cyclohexanone, which on reduction with sodium borohydride or lithium triethyl-borohydride provides access to a wide range of enantiomerically pure N-tert-butylsulfinyl 1,3-amino alcohols with five stereogenic centers.