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Synfacts 2014; 10(8): 0834
DOI: 10.1055/s-0034-1378422
DOI: 10.1055/s-0034-1378422
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
Copper-Catalyzed Enantioselective Mannich Reaction of Cyclic Aldimines
Zhang H.-X, Nie J, Cai H, Ma J.-A * Tianjin University and Collaborative Innovation Center of Chemical Science and Engineering,
Tianjin, P. R. of China
Cyclic Aldimines as Superior Electrophiles for Cu-Catalyzed Decarboxylative Mannich Reaction of β-Ketoacids with a Broad Scope and High Enantioselectivity.
Org. Lett. 2014;
16: 2542-2545
Cyclic Aldimines as Superior Electrophiles for Cu-Catalyzed Decarboxylative Mannich Reaction of β-Ketoacids with a Broad Scope and High Enantioselectivity.
Org. Lett. 2014;
16: 2542-2545
Further Information
Publication History
Publication Date:
18 July 2014 (online)
Significance
The authors demonstrate a decarboxylative Mannich reaction of cyclic aldimines catalyzed by a CuI/Phbox ligand with excellent enantioselectivities. The Z-geometry of the C=N bond in cyclic imines plays a crucial role in the asymmetric induction compared to the acyclic one having E-geometry.
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Comment
This work provides a highly efficient method for the synthesis of optically active β-amino ketones with a broad substrate scope. The obtained products can be converted into biologically useful chroman-4-amines in a simple way.
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