Enantioselective catalytic reduction of ketoimines with trichlorosilane promoted by readily available chiral Lewis bases.
The straightforward synthesis of a series of enantiomerically pure Lewis basic amides by simple condensation of commercially available enantiopure diamines with picolinic acid is reported. These compounds were shown to promote the enantioselective reduction of ketoimines with trichlorosilane. Working with the model substrate N-phenyl benzophenone imine, the new organocatalysts led to the formation of the corresponding amine, with excellent chemical efficiency (up to 99% chemical yield) and good stereoselectivity (up to 73% ee). Up to 83% of enantioselectivity was reached in the reduction of differently substituted imines.
Guizzetti
Stefania
S
Dipartimento di Chimica Organica e Industriale, Universita' di Milano, I-20133 Milano, Italy.
Benaglia
Maurizio
M
Cozzi
Franco
F
Rossi
Sergio
S
Celentano
Giuseppe
G
D002384:Catalysis; D007097:Imines / Q000737:chemistry*; D008968:Molecular Conformation; D010084:Oxidation-Reduction; D012821:Silanes / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity
D007097:Imines; D012821:Silanes; C065893:trichlorosilane