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 Morewebsite:http://www.np-chem.com
Contact:0086-25-52346877
Address:199, Jian Ye Road, Nanjing, China
Anhui Dexinjia Biopharm Co., Ltd
Contact:+86-531-82375818
Address:9 Hexie Road, kaifaqu, Taihe
Shanghai Mio Chemical Co., Ltd
Contact:0086 21- 64401188-622
Address:16 Floor NO.2 Jiefang Building, No. 4855 Dushi Road, 201100 Shanghai, P.R.China
Shanghai shibo Chemical Co., Ltd
Contact:+86-021-60753516
Address:688 Qiushi Road, Jinshan High-tech Park, Shanghai, China,201512
Jiangsu Zenji Pharmaceuticals LTD
Contact:+86-025-83172562; +1-224-888-1133(USA)
Address:No.5 Xinmofan Road
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)