A practical and efficient protocol has been developed to realize the catalytic rearrangement of allyl but-3-enoate to heptadienoic acids in NaHCO3 saturated water, in the presence of catalytic amounts of a rhodium(I) complex, containing olefin, diene or phosphine ligands. The reaction mainly affords the sodium salt of E-2,6-heptadienoic acid, with high catalytic efficiency (3600 TON). A reaction scheme of the process is proposed. The reaction course differs from that observed in organic solvents, where E-3,6-heptadienoic acid is formed predominantly.
Catalysis in water: highly efficient synthesis of heptadienoic acids by rearrangement of allyl but-3-enoate promoted by Rh(I) complexes
GABRIELE, Bartolo;
2007-01-01
Abstract
A practical and efficient protocol has been developed to realize the catalytic rearrangement of allyl but-3-enoate to heptadienoic acids in NaHCO3 saturated water, in the presence of catalytic amounts of a rhodium(I) complex, containing olefin, diene or phosphine ligands. The reaction mainly affords the sodium salt of E-2,6-heptadienoic acid, with high catalytic efficiency (3600 TON). A reaction scheme of the process is proposed. The reaction course differs from that observed in organic solvents, where E-3,6-heptadienoic acid is formed predominantly.File in questo prodotto:
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