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Synfacts 2014; 10(1): 0066
DOI: 10.1055/s-0033-1340435
DOI: 10.1055/s-0033-1340435
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
Palladium-Catalyzed Asymmetric Synthesis of Phosphine Sulfonates
Lu J, Ye J, Duan W.-L * Shanghai Institute of Organic Chemistry and East China University of Science and Technology,
Shanghai, P. R. of China
Palladium-Catalyzed Asymmetric Addition of Diarylphosphines to α,β-Unsaturated Sulfonic Esters for the Synthesis of Chiral Phosphine Sulfonate Compounds.
Org. Lett. 2013;
15: 5016-5019
Palladium-Catalyzed Asymmetric Addition of Diarylphosphines to α,β-Unsaturated Sulfonic Esters for the Synthesis of Chiral Phosphine Sulfonate Compounds.
Org. Lett. 2013;
15: 5016-5019
Further Information
Publication History
Publication Date:
13 December 2013 (online)
Significance
The authors reported the asymmetric conjugate addition of diarylphosphines to sulfonic esters catalyzed by a pincer–palladium complex. In the presence of an electron-withdrawing group in the sulfonic esters, phosphine sulfonates were obtained in high yields.
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Comment
Introducing of heteroatoms into phosphine compounds is interesting since they can be used as ligands in metal-catalyzed transformations. Using this system, a highly enantioselective synthesis of phosphine sulfonates was achieved. The transformation of the product into the palladium complex was also demonstrated.
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