title: Enantioselective Mannich reaction of β-keto esters with aromatic and aliphatic imines using a cooperatively assisted bifunctional catalyst.
abstract: An efficient urea-enhanced thiourea catalyst enables the enantioselective Mannich reaction between β-keto esters and N-Boc-protected imines under mild conditions and minimal catalyst loading (1-3 mol %). Aliphatic and aromatic substituents are tolerated on both reaction partners, affording the products in good enantiomeric purity. The corresponding β-amino ketones can readily be accessed via decarboxylation without loss of enantiomeric purity.
authors.affiliation: Department of Chemistry and NanoScience Center, University of Jyväskylä , Survontie 9B, 40520 Jyväskylä, Finland.
authors.forename: Antti J
authors.initials: AJ
authors.lastname: Neuvonen
authors.forename: Petri M
authors.initials: PM
authors.lastname: Pihko
mesh_terms: D002384:Catalysis; D003653:Decarboxylation; D004952:Esters; D007097:Imines / Q000737:chemistry*; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism; D013890:Thiourea / Q000737:chemistry*; D014508:Urea / Q000737:chemistry*
chemical_list: D004952:Esters; D007097:Imines; D007659:Ketones; D014508:Urea; D013890:Thiourea