Enantiomerically enriched cryptone by lipase catalysed kinetic resolution |
| |
| Affiliation: | 1. Instituto de Investigaciones en Materiales, Universidad Nacional Autónoma de México (UNAM), Circuito Exterior S/N, Cd. Universitaria, C.P. 04510 México, D.F., Mexico;2. Instituto de Investigaciones en Materiales, Unidad Morelia, Universidad Nacional Autónoma de México, Campus Morelia UNAM, Antigua Carretera a Pátzcuaro No. 8701, Col. Ex-Hacienda de San José de la Huerta, C.P. 58190 Morelia, Michoacán, Mexico;1. Department of Chemistry, Faculty of Science, Prince of Songkla University, Hat Yai, Songkhla 90112, Thailand;2. Natural Product Research Center of Excellence, Prince of Songkla University, Hat Yai, Songkhla 90112, Thailand;3. Faculty of Oriental Medicine, Rangsit University, Muang, Pathumthani 12000, Thailand;4. Department of Microbiology, Faculty of Science, Prince of Songkla University, Hat Yai, Songkhla 90112, Thailand;1. Graduate School of Life Sciences, Ritsumeikan University, Kusatsu, Shiga 525-8577, Japan;2. Nagahama Institute of Bio-Science and Technology, Nagahama, Shiga 526-0829, Japan |
| |
| Abstract: | Thiophenol was added to racemic cryptone (4-isopropyl-2-cyclohexene-1-one) and the resulting 1,4-addition products, cis- and trans-4-isopropyl-3-(phenylsulfanyl)cyclohexanone were separated and the latter reduced to rac-1,3-cis-1,4-trans-4-isopropyl-3-(phenylsulfanyl)cyclohexanol, which was subjected to lipase catalysed resolution by acylation catalysed by CAL-B (Candida antarctica lipase B). The alcohol enantiomers obtained were oxidised. The remaining alcohol was separated from the produced acetate, which was hydrolysed to the alcohol. The initial products, probably sulfoxidoketones spontaneously decomposed to furnish enantiomerically enriched (R)- and (S)-cryptone with up to 76% and 98% ee, respectively. |
| |
| Keywords: | |
| 本文献已被 ScienceDirect 等数据库收录！ |
|
