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Enantioselective Mannich Reactions with the Practical Proline Mimetic N-(p-Dodecylphenyl-sulfonyl)-2-pyrrolidinecarboxamide

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journal contribution
posted on 06.03.2009, 00:00 by Hua Yang, Rich G. Carter
A highly enantioselective and diastereoselective protocol for performing Mannich reactions has been developed by using a p-dodecylphenylsulfonamide-based proline catalyst. This catalyst facilitates the use of common, nonpolar solvents and increased concentrations as compared to alternative methods. A series of syn-selective Mannich reactions is reported, including the rapid access of α- and β-amino acids surrogates. The use of the industrially attractive nonpolar solvents, such as 2-methyl-tetrahydrofuran, is also demonstrated.