Asymmetric synthesis of beta-hydroxy acid via stereoselective dirhodium(II)-catalyzed C-H insertion of alpha-alkoxydiazoketone.
A new methodology for the asymmetric synthesis of beta-hydroxy acid was developed. Dirhodium(II)-catalyzed C-H insertion of alpha-alkoxydiazoketone (3), which was prepared from primary alkyl halide (1) and readily available chiral alpha-hydroxy acid (2), gave stereoselectively 2,5-cis-disubstituted 3(2H)-furanone (4). The Baeyer-Villiger reaction of 4 followed by treatment with an acid afforded chiral beta-hydroxy acid (6) with high optical purity.
Yakura
Takayuki
T
Kyoto Pharmaceutical University, Misasagi, Yamashina-ku, Japan. yakura@mb.kyoto-phu.ac.jp
Tanaka
Takeshi
T
Ikeda
Masazumi
M
Uenishi
Jun'ichi
J
D000478:Alkylation; D002384:Catalysis; D006880:Hydroxy Acids / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D012238:Rhodium / Q000737:chemistry* / Q000378:metabolism; D013237:Stereoisomerism
D006880:Hydroxy Acids; D007659:Ketones; D012238:Rhodium