Enantioselective rearrangement of a meso-cyclohexene oxide using norephedrine-derived chiral bases |
| |
| Institution: | 1. Lancaster Synthesis Ltd, Eastgate, White Lund, Morecambe, Lancashire LA3 3DY, UK;2. Department of Chemistry, University of York, Heslington, York YO10 5DD, UK;1. Generic Drug Research Center of Guizhou Province, School of Pharmacy, Zunyi Medical University, Zunyi 563000, PR China;2. National Engineering Research Center of Chiral Drugs, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, PR China;1. Department of Psychology, University of Alberta, Edmonton, Canada;2. Neuroscience and Mental Health Institute, University of Alberta, Edmonton, Canada;1. Department of Neurology, Memory and Aging Center, University of California, San Francisco, USA;2. Department of Radiology and Biomedical Imaging, University of California, San Francisco, USA;3. Department of Veterans Affairs Medical Center, San Francisco, CA, USA;4. Parkinson''s Disease Research, Education, and Clinical Center, San Francisco Veteran''s Affairs Medical Center, San Francisco, USA;1. Department of Cardiology, Nagoya University Graduate School of Medicine, Nagoya, Japan;2. Department of Community Healthcare & Geriatrics, Nagoya University Graduate School of Medicine, Nagoya, Japan;3. Department of Medicine, Brigham and Women''s Hospital, Harvard Medical School, United States;4. Department of Cardiology, Yanbian University Hospital, Yanji, China |
| |
| Abstract: | Using a chiral base from a norephedrine-derived diamine, the enantioselective rearrangement of a meso-cyclohexene oxide can be performed in 94% yield and with 94% enantioselectivity. The enantioselectivity is lower (86% ee) with the diastereoisomeric chiral base. In order to prepare the diastereoisomeric chiral base, a potentially useful way of converting norephedrine into norpseudoephedrine was developed. |
| |
| Keywords: | |
| 本文献已被 ScienceDirect 等数据库收录！ |
|
