Asymmetric synthesis of 3, 5-bis (isopropyloxy)-4-methoxyphenyl glycine by way of a diastereoselective Strecker reaction and an Evans electrophilic amination …

…, JP Bouillon, J Chastanet, M Bois-Choussy, J Zhu

Index: Vergne, Caroline; Bouillon, Jean-Philippe; Chastanet, Jacqueline; Bois-Choussy, Michele; Zhu, Jieping Tetrahedron Asymmetry, 1998 , vol. 9, # 17 p. 3095 - 3103

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Citation Number: 15

Abstract

Two short syntheses of DN-Boc-3, 5-bis (isopropyloxy)-4-methoxyphenyl glycine, a central unit of vancomycin type antibiotics, have been developed. A diastereoselective Strecker reaction using (S)-phenylglycinol as a chiral inducer was the key step in the first synthesis, while Evans' electrophilic amination technology was employed for introducing both the amino function and the chirality in the second strategy.