Cooperative assistance in bifunctional organocatalysis: enantioselective Mannich reactions with aliphatic and aromatic imines.
Hold them tight: Guided by X-ray structures, bifunctional thiourea catalysts containing an activating intramolecular hydrogen bond were redesigned. The new catalysts were used to effect a highly enantioselective Mannich reaction between malonates and both aliphatic and aromatic imines (see scheme; Boc=tert-butoxycarbonyl).
Department of Chemistry, Nanoscience Center, University of Jyväskylä, POB 35, 40014 JYU, Finland.
Nicolas
N
Probst
Adám
A
Madarász
Arto
A
Valkonen
Imre
I
Pápai
Kari
K
Rissanen
Antti
A
Neuvonen
Petri M
PM
Pihko
D000596:Amino Acids / Q000138:chemical synthesis*; D002384:Catalysis; D018360:Crystallography, X-Ray; D006860:Hydrogen Bonding; D007097:Imines / Q000737:chemistry*; D008314:Malonates / Q000737:chemistry*; D008958:Models, Molecular; D013237:Stereoisomerism
D000596:Amino Acids; D007097:Imines; D008314:Malonates