Preparation of optically active 4-substituted γ-lactones by lipase-catalyzed optical resolution

Heterocyclic communications

article

Yasutaka Shimotori¹  Masayuki Hoshi¹  Keita Inoue²  Takeshi Osanai²  Hayato Okabe²  Tetsuo Miyakoshi² 

[1] Department of Biotechnology and Environmental Chemistry, Kitami Institute of Technology;Department of Applied Chemistry, School of Science and Technology, Meiji University

关键词: enantioselective acetylation;    enzymatic resolution;    Grignard reaction;    γ-lactone;    organolithium reagent;   

DOI  :  10.1515/hc-2015-0027

学科分类：内科医学

来源: De Gruyter

【 摘 要 】

Optically active 4-substituted γ-lactones ( 3 and 4 ) were synthesized effectively using lipase-catalyzed optical resolution. N -methyl-4-hydroxyalkanamides ( rac - 1a – i ) as substrates were prepared from N -methylsuccinimide. The alkylation of N -methylsuccinimide using Grignard reagents generated from various alkyl halides followed by reduction resulted in N -methyl-4-hydroxyalkanamides. The optical resolution of rac - 1a – g was performed using Novozym 435-catalyzed stereoselective acetylation. The stereoselective preparation of 4-substituted γ-lactones ( 3 and 4 ) possessing various side chains such as isopentyl, phenyl, and phenethyl groups was achieved with more than 90% enantiopurity.

【 授权许可】

CC BY|CC BY-NC-ND