DIASTEREOSELECTIVE CONJUGATE 1,6-ADDITION OF LITHIUM AMIDES TO NAPHTHYLOXAZOLINES - MECHANISTIC STUDIES AND SYNTHESIS OF DELTA-AMINO ACID-DERIVATIVES

The novel 1,6-amino addition reaction to the naphthalene ring system f ollowed by the electrophilic alkylation is presented. The detailed mec hanistic studies suggest the existence of two equilibrations that resu lt in the 1,4-amino addition reaction and the 1,6-amino addition react ion. The stability and bulkiness of lithium amide play a key role in d irecting the course of the reaction. The transformation of the 1,6-ami no adducts to other useful compounds is concisely demonstrated. The me thodology provides a remote-controlled diastereoselective synthesis of 6-amino acid derivatives. (C) 1998 Elsevier Science Ltd. All rights r eserved.