From serine to functionalized enantiopure tetrahydroisoquinolines

The reaction of gamma-amino-alpha,beta-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. (C) 2000 Elsevier Science Ltd. All rights reserved.