Base-catalyzed three-component direct Mannich reaction of enolizable ketones with high syn-selectivities |
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Authors: | Qunsheng GuoJohn Cong-Gui Zhao Hadi Arman |
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Institution: | Department of Chemistry, University of Texas at San Antonio, One UTSA Circle, San Antonio, TX 78249-0698, USA |
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Abstract: | 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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Keywords: | Mannich reaction Diastereoselective Catalysis β-Aminoketone Ketones 1 1 3 3-Tetramethylguanidine |
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