| Autor: |
Sibanarayan Tripathy, Angshuman Chattopadhyay |
| Rok vydání: |
2012 |
| Předmět: |
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| Zdroj: |
Tetrahedron: Asymmetry. 23:1423-1429 |
| ISSN: |
0957-4166 |
| DOI: |
10.1016/j.tetasy.2012.09.007 |
| Popis: |
(R)-2,3-O-Cyclohexylideneglyceraldehyde 1 provides a simple route for the preparation of carbafuranoses. This has been exemplified by the preparation of 10c and 10d, the derivatives of carba d -xylofuranose and carba- l -arabinofuranose respectively, starting from homoallylic alcohol 2a derived from 1. The key step in this protocol was the intramolecular allylation of 9 promoted by several metals under wet conditions that resulted in the construction of the carbafuranose skeleton of 10. The potential of several metals regarding the efficacy and stereoselectivity of this crucial intramolecular allylation reaction has been studied. The moderate stereoselectivity in all of the successful intramolecular allylations of 9 yielding both d -10c and l -10d as the major products contributed significantly in attaining stereo-divergence in this route. The utility of this route was due to the easy availability of 1, and the operational simplicity as well as scalability of all of the reactions involved. |
| Databáze: |
OpenAIRE |
| Externí odkaz: |
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