| Autor: |
Deardorff DR; Department of Chemistry, Occidental College, Los Angeles, California 90041., Savin KA, Justman CJ, Karanjawala ZE, Sheppeck II JE, Hager DC, Aydin N |
| Jazyk: |
angličtina |
| Zdroj: |
The Journal of organic chemistry [J Org Chem] 1996 May 31; Vol. 61 (11), pp. 3616-3622. |
| DOI: |
10.1021/jo951510s |
| Abstrakt: |
A two-step reaction sequence to homoallylic nitro compounds from allylic alcohols is presented. Ethoxy carbonylation of the alcohols with ethyl chloroformate provides the corresponding allylic ethyl carbonates in high yields. Exposure of these substrates to catalytic palladium(0) in CH(3)NO(2) initiates a reaction sequence, ionization-decarboxylation-nitromethylation, that culminates with the formation of nitroalkenes. The regio- and stereochemical outcomes of the nitromethyl allylation reaction can be explained by the behavior of the transient pi-allylpalladium complexes. This methodology serves as a centerpiece for the synthesis of an important carbocyclic nucleoside intermediate. |
| Databáze: |
MEDLINE |
| Externí odkaz: |
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