Cooperative Assistance in Bifunctional Organocatalysis: Enantioselective Mannich Reactions with Aliphatic and Aromatic Imines

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; B...

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Veröffentlicht in:Angewandte Chemie International Edition 2012-08, Vol.51 (34), p.8495-8499
Hauptverfasser: Probst, Nicolas, Madarász, Ádám, Valkonen, Arto, Pápai, Imre, Rissanen, Kari, Neuvonen, Antti, Pihko, Petri M.
Format: Artikel
Sprache:eng
Schlagworte:
Aliphatic compounds
Amino Acids - chemical synthesis
asymmetric catalysis
Catalysis
Catalysts
Crystallography, X-Ray
Enantiomers
Hydrogen Bonding
Hydrogen bonds
Imines
Imines - chemistry
Malonates - chemistry
Mannich reactions
Models, Molecular
organocatalysis
Stereoisomerism
Thioureas
X-rays
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Zusammenfassung: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).
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201203852