ASYMMETRIC-SYNTHESIS OF 3,5-BIS(ISOPROPYLOXY)-4-METHOXYPHENYL GLYCINEBY WAY OF A DIASTEREOSELECTIVE STRECKER REACTION AND AN EVANS ELECTROPHILIC AMINATION REACTION

Two short syntheses of D-N-Boc-3,5-bis(isopropyloxy)-4-methoxyphenyl g lycine, a central unit of vancomycin type antibiotics, have been devel oped. A diastereoselective Strecker reaction using (S)-phenylglycinol as a chiral inducer was the key step in the first synthesis, while Eva ns' electrophilic amination technology was employed for introducing bo th the amino function and the chirality in the second strategy. (C) 19 98 Elsevier Science Ltd. All rights reserved.