Stereoselective synthesis of 3-heteroaromatic-substituted alanines |
| |
| Institution: | 1. State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, No. 555, Zu Chong Zhi Road, Zhangjiang Hi-Tech Park, Shanghai 201203, China;2. Ocean College, Zhejiang University, Hangzhou 310058, China;3. Open Studio for Druggability Research of Marine Natural Products, Pilot National Laboratory for Marine Science and Technology (Qingdao), 1 Wenhai Road, Aoshanwei, Jimo, Qingdao 266237, China;1. Department of Chemistry, Dibrugarh University, Dibrugarh, Assam, India;2. Department of Chemistry, CICECO-Aveiro Institute of Materials, University of Aveiro, Aveiro, Portugal;1. Institute of Molecular Biology, Bulgarian Academy of Sciences, Acad. G. Bonchev Street, Bl. 21, Sofia 1113, Bulgaria;2. J. Heyrovský Institute of Physical Chemistry, Czech Academy of Sciences, Dolejškova 3,182 23 Praha 8, Czech Republic |
| |
| Abstract: | An asymmetric synthesis of (R)-3-heterocyclic-substituted alanines starting from (2S)-(+)-2,5-dihydro-3,6-dimethoxy-2-isopropylpyrazine (Schöllkopf reagent) and heteroaromatic halogenomethyl derivatives via hydrolysis of intermediate adducts is reported. The diastereocontrolled addition gives mainly compounds with the (2S,5R) configuration whose formation is explained on the basis of the accepted model for the alkylation reaction of the Schöllkopf reagent, and structure confirmed by spectroscopic data. |
| |
| Keywords: | |
| 本文献已被 ScienceDirect 等数据库收录！ |
|
