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- W2082334963 abstract "Enhancing atom economy of the metal-catalyzed asymmetric allylic alkylation (AAA) shifts from the usual nucleophilic displacement of a leaving group to an addition of a pronucleophile to a double bond. Using 1-alkoxyallenes as proelectrophiles, the palladium-catalyzed AAA proceeds with 1,3-dicarbonyl compounds as pronucleophiles with excellent regioselectivity and enantiomeric excess under optimized conditions. The pH of the medium proved crucial for reactivity/selectivity. By using the more acidic Meldrum's acids, the reactions required a co-catalytic amount of Brønsted acid, such as trifluoroacetic acid. Single regioisomeric products of 82-99 % ee were obtained. On the other hand, the less acidic 1,3-diketones failed to react under such conditions. The fact that a less acidic acid like benzoic acid sufficed, suggested the need for general base catalysis as well. Thus, a mixture of triethylamine and benzoic acid proved optimal (ee's 93-99). Employment of the (R,R)-phenyl Trost ligand gave a product with S configuration. A model to rationalize the results has been developed." @default.
- W2082334963 created "2016-06-24" @default.
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- W2082334963 date "2005-11-18" @default.
- W2082334963 modified "2023-09-29" @default.
- W2082334963 title "Enantioselective Palladium-Catalyzed Addition of 1,3-Dicarbonyl Compounds to an Allene Derivative" @default.
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- W2082334963 doi "https://doi.org/10.1002/chem.200500826" @default.
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