Synthesis of a Chiral α-(Aminooxy) arylacetic Ester. I. A Route through Optical Resolution of a Racemic α-(Phthalimidooxy) arylacetic Acid

H Iwagami, M Nakazawa, M Yatagai, T Hijiya…

Index: Iwagami; Nakazawa; Yatagai; Hijiya; Honda; Naora; Ohnuki; Yukawa Bulletin of the Chemical Society of Japan, 1990 , vol. 63, # 11 p. 3073 - 3081

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Citation Number: 13

Abstract

A synthetic route has been developed to the synthesis of a chiral O-alkyloxime (S)-16, which can be a synthetic intermediate for a potent antipsedomonal cephalosporin antibiotic M- 14659 (1). The oxime moiety in (S)-16 has a chiral center at the carbon atom adjacent to the oxygen atom. We have achieved that (S)-16 can be prepared via t-butyl 2-aminooxy-2-[3, 4- (isopropylidenedioxy) phenyl] acetate [(S)-15] from an optically active α-(phthalimidooxy) ...