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EnglishThe cerium(III)chloride heptahydrate/so- dium iodide complex (CeCl3 ·7H2 O/NaI)acts as a useful promoter in the carbon-carbon bond forming reaction by addition of allyltributylstannanes to alde- hydes.The reaction of 2-butenyltributylstannane shows that the regio-and the stereochemical out- comes depend on the reaction conditions.When the promoter is adsorbed on a solid support (aluminum oxide),a highly prevalent formation of the g -adduct is observed in solvent-free conditions.Conversely, when the reaction is carried out in acetonitrile as the solvent,the a -adduct largely prevails.In the last case,a complete stereocontrol is observed,the less stable (Z )-isomer being obtained in high geometrical purity.
| Titolo: | Allylation of Aldehydes Promoted by the CeCl3.7H2O/NaI System: the Dependence of Regio- and Stereocontrol from the Reaction Conditions | |
| Autore/i: | BARTOLI, GIUSEPPE; A. Giuliani; E. Marcantoni; MASSACCESI, MASSIMO; MELCHIORRE, PAOLO; S. Lanari; SAMBRI, LETIZIA | |
| Autore/i Unibo: | ||
| Anno: | 2005 | |
| Rivista: | ||
| Digital Object Identifier (DOI): | http://dx.doi.org/10.1002/adsc.200505184 | |
| Abstract: | The cerium(III)chloride heptahydrate/so- dium iodide complex (CeCl3 ·7H2 O/NaI)acts as a useful promoter in the carbon-carbon bond forming reaction by addition of allyltributylstannanes to alde- hydes.The reaction of 2-butenyltributylstannane shows that the regio-and the stereochemical out- comes depend on the reaction conditions.When the promoter is adsorbed on a solid support (aluminum oxide),a highly prevalent formation of the g -adduct is observed in solvent-free conditions.Conversely, when the reaction is carried out in acetonitrile as the solvent,the a -adduct largely prevails.In the last case,a complete stereocontrol is observed,the less stable (Z )-isomer being obtained in high geometrical purity. | |
| Data prodotto definitivo in UGOV: | 2006-02-08 10:08:59 | |
| Appare nelle tipologie: | 1.01 Articolo in rivista |
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http://hdl.handle.net/11585/22892
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