From serine to functionalized enantiopure tetrahydroisoquinolines

The reaction of γ-amino-α,β-unsaturated esters prepared from l-serine with diversely substituted arylcuprates affords the corresponding syn-adducts. Transformation of the amino group to an isocyanate, followed by Friedel–Crafts intramolecular condensation, leads to enantiopure 3,4-disubstituted tetrahydroisoquinolin-1-ones, which can be reduced to the corresponding tetrahydroisoquinolines.