对称化
烯酮
立体中心
化学
对映选择合成
手性助剂
组合化学
水解
羧酸
有机化学
立体化学
催化作用
作者
Takafumi Yamagami,Noriaki Moriyama,Masahiro Kyuhara,Atsushi Moroda,Takeshi Uemura,Hiroaki Matsumae,Yasunori Moritani,Isao Inoue
摘要
Process research and development for a synthesis of the chiral carboxylic acid (R)-2 as a key intermediate of the glucokinase activator (R)-1 is described. The construction of the stereocenter at the α-carbon is a key point for the synthesis of (R)-2. The proposed process utilizes desymmetrization of a ketene in situ generated from the corresponding racemic carboxylic acid Rac-2 with (R)-pantolactone as a chiral auxiliary followed by hydrolysis of the resulting ester. This key step has been successfully scaled up to 20 kg, which demonstrates that this synthetic approach is comparable with a previously reported approach via enantioselective hydrogenation.
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