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A Divergent Synthetic Strategy Based on the Regioselective Reductive Ring-Opening of a Cyclic 1,2-p-Methoxybenzylidene Acetal
| Content Provider | Scilit |
|---|---|
| Author | Salom-Roig, Xavier J. Géant, Pierre-Yves Martínez, Jean Rocard, Lou |
| Copyright Year | 2012 |
| Description | (1S)-N,N-Dibenzyl-1-[(4R)-2-(4-methoxyphenyl)-1,3-dioxolan-4-yl]ethanamine is obtained in five steps from an α-bromo-α′-(R)-sulfinyl ketone and is used as a common intermediate for the synthesis of the p-methoxybenzyl-protected primary and secondary alcohols, (2R,3S)-3-(dibenzylamino)-2-[(4-methoxybenzyl)oxy]butan-1-ol and (2R,3S)-3-(benzylamino)-1-[(4-methoxybenzyl)oxy]butan-2-ol, respectively. These alcohols are further exploited as precursors for the synthesis of a fully protected syn-3-amino-2-hydroxybutanoic acid and an N-benzyl 2-hydroxymethylaziridine. |
| Related Links | http://www.thieme-connect.de/products/ejournals/pdf/10.1055/s-0031-1289746.pdf |
| Ending Page | 1252 |
| Page Count | 6 |
| Starting Page | 1247 |
| ISSN | 00397881 |
| e-ISSN | 1437210X |
| DOI | 10.1055/s-0031-1289746 |
| Journal | Synthesis |
| Issue Number | 08 |
| Volume Number | 44 |
| Language | English |
| Publisher | Georg Thieme Verlag KG |
| Publisher Date | 2012-03-15 |
| Access Restriction | Open |
| Subject Keyword | Journal: Synthesis Organic Chemistry Protecting Groups Neighboring-group Effects |
| Content Type | Text |
| Resource Type | Article |
| Subject | Organic Chemistry Catalysis |
