Enantioselective Mannich reactions with the practical proline mimetic N-(p-dodecylphenyl-sulfonyl)-2-pyrrolidinecarboxamide.
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 alpha- and beta-amino acids surrogates. The use of the industrially attractive nonpolar solvents, such as 2-methyl-tetrahydrofuran, is also demonstrated.
Yang
Hua
H
Department of Chemistry, Oregon State University, 153 Gilbert Hall, Corvallis, Oregon 97331, USA.
Carter
Rich G
RG
D002384:Catalysis; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry; D018716:Molecular Mimicry; D015394:Molecular Structure; D011392:Proline / Q000737:chemistry*; D011759:Pyrrolidines / Q000737:chemistry*; D013237:Stereoisomerism; D013450:Sulfones / Q000737:chemistry*
D007659:Ketones; C533379:N-(p-dodecylphenylsulfonyl)-2-pyrrolidinecarboxamide; D011759:Pyrrolidines; D013450:Sulfones; D011392:Proline