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Addition of 2-Lithiofuran to Chiral α-Alkoxy Nitrones; a Stereoselective Approach to α-Epimeric β-Alkoxy-α-amino Acids
| Content Provider | Scilit |
|---|---|
| Author | Dondoni, A. Junquera, F. Merino, P. Tejero, T. |
| Editor | Merchan, F. L. |
| Copyright Year | 1994 |
| Description | The addition of 2-lithiofuran (1) to the N-benzyl nitrones 2a-d, derived from chiral α-alkoxy aldehydes, affords β-alkoxy-α-hydroxyamino-2-alkylfurans in good yields and with syn selectivity. Conversely, the reaction with the same nitrones precomplexed with diethylaluminum chloride leads to the same adducts but with anti selectivity. Three pairs of epimeric hydroxylamines are subjected to reductive N-dehydroxylation with titanium(III) chloride and then to furyl-carboxylic acid conversion with ruthenium tetroxide to give the corresponding α-epimeric β-alkoxy-α-amino acids. |
| Related Links | http://www.thieme-connect.de/products/ejournals/pdf/10.1055/s-1994-25712.pdf |
| Ending Page | 1456 |
| Page Count | 7 |
| Starting Page | 1450 |
| ISSN | 00397881 |
| e-ISSN | 1437210X |
| DOI | 10.1055/s-1994-25712 |
| Journal | Synthesis |
| Issue Number | 12 |
| Volume Number | 1994 |
| Language | English |
| Publisher | Georg Thieme Verlag KG |
| Publisher Date | 1994-01-01 |
| Access Restriction | Open |
| Subject Keyword | Journal: Synthesis Organic Chemistry Β Alkoxy Α |
| Content Type | Text |
| Resource Type | Article |
| Subject | Organic Chemistry Catalysis |
