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DOI: 10.1055/s-0033-1341185
Chiral Sulfoxide-P Ligands for Palladium-Catalyzed Asymmetric Allylic Alkylation
Rational Design of Sulfoxide–Phosphine Ligands for Pd-Catalyzed Enantioselective Allylic Alkylation Reactions.
Chem. Commun. 2014;
50: 2873-2875
Publication History
Publication Date:
17 April 2014 (online)
Significance
The asymmetric allylic alkylation is one of the most studied reactions employing a wide spectrum of metal complexes and nucleophiles. The authors report the design of a sulfoxide-phosphine ligand for the palladium-catalyzed asymmetric allylic alkylation of malonates and keto esters furnishing products in high yields and high enantioselectivities.
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Comment
The sulfoxide-phosphine ligand was found to be highly efficient for this type of transformation. In general, the corresponding products were obtained in excellent yields (up to 97%) and enantioselectivities (97–99%), respectively. The substrate scope covers malonates and keto esters as nucleophiles. In the case of methyl-substituted keto esters, the ligand has shown to have little influence at the α-stereogenic center and mixtures of diastereomers were obtained. Variation on the electrophilic component was exploited by introducing substituents on the para position of both aryl groups. Future work regarding sulfoxide-phosphine ligands should notably focus on more challenging unsymmetrical substrates.
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