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.

G. Bartoli, A. Giuliani, E. Marcantoni, M. Massaccesi, P. Melchiorre, S. Lanari, et al. (2005). Allylation of Aldehydes Promoted by the CeCl3.7H2O/NaI System: the Dependence of Regio- and Stereocontrol from the Reaction Conditions. ADVANCED SYNTHESIS & CATALYSIS, 347, 1673-1680 [10.1002/adsc.200505184].

Allylation of Aldehydes Promoted by the CeCl3.7H2O/NaI System: the Dependence of Regio- and Stereocontrol from the Reaction Conditions

BARTOLI, GIUSEPPE;MASSACCESI, MASSIMO;MELCHIORRE, PAOLO;SAMBRI, LETIZIA
2005

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.
2005
G. Bartoli, A. Giuliani, E. Marcantoni, M. Massaccesi, P. Melchiorre, S. Lanari, et al. (2005). Allylation of Aldehydes Promoted by the CeCl3.7H2O/NaI System: the Dependence of Regio- and Stereocontrol from the Reaction Conditions. ADVANCED SYNTHESIS & CATALYSIS, 347, 1673-1680 [10.1002/adsc.200505184].
G. Bartoli; A. Giuliani; E. Marcantoni; M. Massaccesi; P. Melchiorre; S. Lanari; L. Sambri
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11585/22892
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