N-(p-dodecylphenylsulfonyl)-2-pyrrolidinecarboxamide: a practical proline mimetic for facilitating enantioselective aldol reactions.
A highly practical and readily available proline surrogate has been developed with improved solubility properties in common, nonpolar organic solvents. This sulfonamide-based catalyst has proven highly effective at facilitating enantioselective and diastereoselective aldol reactions with a range of substrates in nonpolar organic solvents in the presence of a single equivalent of water. Additionally, catalyst loading as low as 2 mol % can be employed in the absence of any organic solvent with continued high levels of selectivity.
Yang
Hua
H
Department of Chemistry, Oregon State University, 153 Gilbert Hall, Corvallis, Oregon 97331, USA.
Carter
Rich G
RG
D000447:Aldehydes / Q000737:chemistry*; D040761:Biomimetic Materials / Q000737:chemistry*; D002384:Catalysis; D015394:Molecular Structure; D011392:Proline / Q000737:chemistry; D011759:Pyrrolidines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013449:Sulfonamides / Q000737:chemistry; D013450:Sulfones / Q000138:chemical synthesis* / Q000737:chemistry
D000447:Aldehydes; C533379:N-(p-dodecylphenylsulfonyl)-2-pyrrolidinecarboxamide; D011759:Pyrrolidines; D013449:Sulfonamides; D013450:Sulfones; C116609:3-hydroxybutanal; D011392:Proline