HIGHLY REGIO- AND DIASTEREOSELECTIVE FRIEDEL-CRAFTS ALKYLATION OF PHENOLS WITH α-AMINO ALDEHYDES. SYNTHESIS OF OPTICALLY ACTIVE EPHEDRINE-LIKE COMPOUNDS

Article abstract of DOI:10.1016/S0040-4039(01)80376-2

The first direct diastereoselective synthesis of ephedrine-like compounds has been achieved by alkylation of metal phenolates with N-tert-butoxycarbonyl-α-amino aldehydes; β-amino-ortho-hydroxybenzyl alcohols were obtained with good to excellent diastereoselection.