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Hisao Iwagami, Masanobu Yatagai, Masakazu Nakazawa, Haruo Orita, Yutaka Honda, Takashi Ohnuki, Toshihide Yukawa, Synthesis of a Chiral α-(Aminooxy)arylacetic Ester. II. A Route through a Chiral 2-Hydroxy-2-phenylacetic Acid Derivative, Bulletin of the Chemical Society of Japan, Volume 64, Issue 1, January 1991, Pages 175–182, https://doi.org/10.1246/bcsj.64.175
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Abstract
A simple and practical synthetic route has been developed for the synthesis of a chiral α-(aminooxy) ester (S)-16, which is a synthetic intermediate for a potent antipseudomonal cephalosporin antibiotic M-14659. In this synthetic route, the key intermediate is α-hydroxy acid (R)-7 (100%ee), which is prepared by an asymmetric reduction of α-keto ester with NaBH4-(R,R)-tartaric acid followed by a hydrolysis and an optical resolution using l-Leu–NHNH2. (S)-16 is obtained stereoselectively through 3 steps from (R)-7. HPLC analyses and NMR studies have proved that the (S)-16 thus prepared is completely optically pure.