Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 347, Issue 11-13, Pages 1673-1680Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.200505184
Keywords
allylation; cerium; diastereoselectivity; Lewis acids; stannanes; synthetic methods
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The cerium(III) chloride heptahydrate/sodium iodide complex (CeCl3 - 7 H2O/Nal) acts as a useful promoter in the carbon-carbon bond forming reaction by addition of allyltributylstannes to aldehydes. The reaction of 2-butenyltributylstarmane shows that the regio- and the stereochemical outcomes depend on the reaction conditions. When the promoter is adsorbed on a solid support (aluminum oxide), a highly prevalent formation of the gamma-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.
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