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20.2.1.8.15.1.2 Catalytic α-Allylation of Carboxylic Acids

DOI: 10.1055/sos-SD-120-00214

Sawamura, M.; Shimizu, Y.Science of Synthesis Knowledge Updatesearly view.

The catalytic α-allylation of carbonyl compounds is of great importance in organic chemistry because of the synthetic versatility of the allyl group. Transition-metal-catalyzed reactions via π-allylmetal species have been extensively studied for asymmetric α-allylation,[‌10‌‌15‌] and application to carboxylic acids is possible under palladium/boron hybrid catalysis, using allyl acetate as an allylating agent under mild, basic conditions (DBU or N-methylpyrrolidine) (Scheme 2).[‌16‌] The use of chiral ligand 3 on the palladium catalyst along with chiral ligand 4 on the boron catalyst tetraacetoxy diboroxane is important for obtaining the chiral α-allylated carboxylic acid products 5 in good yields with high enantioselectivities.

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References


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