Evaluation of enantioselectivity in lipase-catalyzed acylation of hydroxyalkylphosphine oxides |
| |
Authors: | Kosei Shioji Takafumi Ueyama Nobuaki Ueda Emiko Mutoh Tsutomu Kurisaki Hisanobu Wakita Kentaro Okuma |
| |
Affiliation: | aDepartment of Chemistry, Faculty of Science, Fukuoka University, Jonan-ku, Fukuoka 814-0180, Japan |
| |
Abstract: | The lipase-catalyzed optical resolution of 2-, 3-, and 5-hydroxyalkyl phosphorus compounds 1 provided the corresponding optically pure diastereomers in good yields. (SP, R)- and (RP, S)-1 were acylated faster than (SP, S)- and (RP, R)-1. The stereoselectivity at the phosphorus atom changed with the flexibility of the active sites in the lipases. The stereoselectivity at the phosphorus atom was higher in the reaction of 1a than in the reaction of 1b,c. The reaction rate of -hydroxyalkylphosphine oxide 1c was faster than that of 1a, although less enantioselectivity was observed at the phosphorus atom. |
| |
Keywords: | Lipase Optical resolution Hydroxyalkylphosphine oxides |
本文献已被 ScienceDirect 等数据库收录! |
|