Synthesis of ¥á-Ketobutyrolactones and ¥ã-Hydroxy-¥á-Keto Acids

Bulletin of the Korean chemical society

Yumi Ji¹  Ji-Yeon Yu¹  Sang-Joon Lee¹  Yeon-Kwon Yu¹  Han-Young Kang¹  Younghoon Lee¹ 

关键词: ¥á-Ketobutyrolactones;    ¥ã-Hydroxy-¥á-keto acids;    Indium;    Enzymes;    Enantiomeric resolution;   

DOI  :  

学科分类：化学（综合）

来源: Korean Chemical Society

【 摘 要 】

In connection with the studies for developing new enzymes that could be useful in organic synthesis, practical preparation of racemic and enantiopure forms of �?-hydroxy-�?-keto acids has been successfully achieved. For racemic form of �?-hydroxy-�?-keto acids, indium-mediated allylation of aldehydes with 2-(bromomethyl)acrylic acid has been employed as a key step. Oxidative cleavage of the thus formed 2-methylenebutyrolactones provided the desired �?-ketobutyrolactones. Enzymatic resolution of the �?-hydroxy-�?-methylene esters provided the desired �?-hydroxy-�?-methylene acids which were successfully converted to �?-hydroxy-�?-ketobutyrolactones in optically pure forms.

【 授权许可】

Unknown