Base-catalyzed three-component direct Mannich reaction of enolizable ketones with high syn-selectivities

Guo, Qunsheng; Zhao, John Cong-Gui; Arman, Hadi

Base-catalyzed three-component direct Mannich reaction of enolizable ketones with high syn-selectivities

2012

Guo, Qunsheng | Zhao, John Cong-Gui | Arman, Hadi

The three-component direct Mannich reaction between aldehydes, p-toluenesulfonamide, and enolizable ketones was achieved for the first time with organic bases as the catalysts. The corresponding N-tosylated β-aminoketones were obtained in high yields and good to excellent diastereoselectivities using TMG as the catalyst. Through reduction of the ketone group, the reaction product may be converted into β-aminol with excellent diastereoselectivity.

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