Synthesis and N-functionalization of isoxazolidines: a new approach to nucleoside analogues |
| |
| Authors: | Carlos AD Sousa José E Rodríguez-Borges Xerardo Garcia-Mera |
| |
| Institution: | 1. REQUIMTE, Departamento de Química e Bioquímica, Universidade do Porto, Rua do Campo Alegre, 4169-007 Porto, Portugal;2. Centro de Investigação em Química, Departamento de Química e Bioquímica, Universidade do Porto, Rua do Campo Alegre, 4169-007 Porto, Portugal;3. Departamento de Química Orgánica, Facultade de Farmacia, Universidade de Santiago de Compostela, E-15782 Santiago de Compostela, Spain |
| |
| Abstract: | A straightforward synthetic approach for the preparation of non N-functionalized isoxazolidines from BF3-catalyzed 1,3-cycloaddition reactions between methyl glyoxylate oxime and alkenes is described. Subsequently, isoxazolidines were N-functionalized with three chemically active groups (2-chloroethyl, cyanomethyl and 2-acetoxyethyl), thus allowing the preparation of a wide array of N-functionalized isoxazolidines. The compounds were characterized by means of 1H and 13C NMR spectroscopy and mass spectrometry. X-ray analysis was used for stereochemical elucidation. |
| |
| Keywords: | 1 3-Cycloaddition Azasugars Alkylation Isoxazolidines N-Functionalization |
| 本文献已被 ScienceDirect 等数据库收录！ |
|
