Tetrahedron p. 4775 - 4794 (1994)
Update date:2022-07-31
Topics:
Faber, Wijnand S.
Kok, Johan
De Lange, Ben
Feringa, Ben L.
The kinetic resolution of racemic 5-alkoxy-2(5H)-furanones, using a chiral aminoalcohol catalyzed 1,4-addition of arylthiols, was examined. Using various butenolides it was shown that a γ-alkoxy substituent appears to be essential to reach high enantioselectivities whereas electron-donating substituents in the arylthiols also increase the selectivity. Cinchona alkaloids are the preferred catalysts for the kinetic resolution, with quinine and quinidine leading to the most efficient and selective thiol additions. A remarkable dilution effect and a strong dependency on the mode of addition of reactants were observed. Optimization studies are presented of the kinetic resolution of 5-methoxy-2(5H)-furanone 2 resulting in (R)-2 or (S)-2 with enantiomeric excesses exceeding 90%. A mechanism for the quinine (quinidine) catalyzed kinetic resolution is given.
View MoreBeijing Merson Pharmaceutical Co., Ltd
Contact:0086-10-80484934 0086-10-80484574/
Address:2nd Floor , No. 2 Building , No. 14 Houshayu Duan, Jingmi Road ,Shunyi District , Beijing 101318, P.R.China
Huangshi Meifeng Chemical Co.,ltd.
Contact:+86-714-6516706
Address:1941-4-3#,Hubin Avenue,Huangshi,Hubei,China
Xi'an North Information Industry Co., Ltd. Weilv Chemical Department
Contact:+86-29-88156413
Address:Jixiang Road 99 Xi'an Shaanxi Province
Frapp's Chemical (NFTZ) Co.,Ltd
Contact:+86-576-86137892
Address:General Chamber of Commercial Building, 159 Wanchang Middle Road, Wenling, Zhejiang, China
Tianjin Ji Ping Jia Chemical Co., Ltd.
Contact:18622448868
Address:tianjin
Doi:10.1021/ja00159a042
(1990)Doi:10.1016/S0040-4039(00)96027-1
(1987)Doi:10.1016/j.jorganchem.2008.11.021
(2009)Doi:10.1021/jo00256a035
(1988)Doi:10.1021/jm00399a034
(1988)Doi:10.1016/S0040-4039(00)96819-9
(1987)