Synthesis of enantiomerically pure (R)- and (S)-2-ethoxycarbonylmethyl-2-hydroxy-cyclohexanones |
| |
| Institution: | 1. Dpto de Quı́mica Orgánica, Universidad Autónoma de Madrid, Cantoblanco, 28049 Madrid, Spain;2. Dpto de Quı́mica Orgánica y Farmacéutica, Facultad de Farmacia, Universidad de Sevilla, Spain;1. Kazan (Volga Region) Federal University, Kremlyovskaya 18, Kazan 420008, Russia;2. A.E. Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center of RAS, Arbuzov str. 8, Kazan 420088, Russia;1. Division of Applied Chemistry, Graduate School of Engineering, Tokyo University of Agriculture and Technology, 2-24-16 Nakamachi, Koganei 184-8588, Japan;2. Department of Biomolecular Functional Engineering, Ibaraki University, Nakanarusawa 4-12-1, Hitachi 316-8511, Japan;3. Department of Chemistry, Faculty of Science, Ochanomizu University, Otsuka, Bunkyo-ku, Tokyo 112-8610, Japan;1. State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, China;2. Institute of Marine Biomedicine, Shenzhen Polytechnic, Shenzhen 518055, China;3. State Key Laboratory of Chemical Oncogenomics, Shenzhen Engineering Laboratory of Nano Drug Slow-Release, Peking University Shenzhen Graduate School, Shenzhen 518055, China;4. School of Food and Biological Engineering, Shaanxi University of Science and Technology, Xi''an 710021, China;1. Department of Chemistry and Biochemistry, The University of Arizona, Tucson, AZ 85721, USA;2. Department of Chemistry, The University of Kansas, Lawrence, KS 66045, USA |
| |
| Abstract: | Sulfenylation of 2-p-tolylsulfinyl cyclohexanone can be achieved at −78°C with thiosulfonates. The in situ aldol reaction of these compounds with ethyl acetate enolate is highly stereoselective (1,2-asymmetric induction) and yields diastereomeric mixtures of β-hydroxyesters (the configuration of the major one being dependent on the sulfenylating agent) that can be readily separated and transformed into the enantiomerically pure title ketones. |
| |
| Keywords: | |
| 本文献已被 ScienceDirect 等数据库收录！ |
|
