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Synfacts 2016; 12(1): 0047
DOI: 10.1055/s-0035-1561018
DOI: 10.1055/s-0035-1561018
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
Palladium-Catalyzed Enantioselective 1,2-Difunctionalization of 1,3-Dienes
Wu X, Lin H.-C, Li M.-L, Li L.-L, Han Z.-Y, Gong L.-Z * University of Science and Technology of China, Hefei and Collaborative Innovation Center of Chemical Science and Engineering, Tianjin, P. R. of China
Enantioselective 1,2-Difunctionalization of Dienes Enabled by Chiral Palladium Complex-Catalyzed Cascade Arylation/Allylic Alkylation Reaction.
J. Am. Chem. Soc. 2015;
137: 13476-13479
Enantioselective 1,2-Difunctionalization of Dienes Enabled by Chiral Palladium Complex-Catalyzed Cascade Arylation/Allylic Alkylation Reaction.
J. Am. Chem. Soc. 2015;
137: 13476-13479
Further Information
Publication History
Publication Date:
16 December 2015 (online)
Key words
dienes - difunctionalization - palladium - asymmetric catalysis - cascade reaction - arylation
Significance
The authors report a palladium-catalyzed enantioselective three-component coupling of 1,3-dienes with aryl iodides and sodium dialkylmalonates by using a H8-BINOL-based phosphoramidite ligand. A series of chiral 1,2-difunctionalized products were prepared in good yields (≤93%) with high regio- and enantioselectivities (15:1 or better and ≤98% ee).
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Comment
This reaction proceeds by a palladium-catalyzed cascade arylation and asymmetric allylic alkylation reaction, which provides an important alternative strategy for the enantioselective difunctionalization of 1,3-dienes, leading to synthetically useful chiral chemicals.
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