Organocatalysis with a fluorous tag: asymmetric reduction of imines with trichlorosilane catalyzed by amino acid-derived formamides.
Asymmetric reduction of ketimines 1 with trichlorosilane can be catalyzed by N-methylvaline-derived Lewis-basic formamides 3a-d with high enantioselectivity (< or =95% ee) and low catalyst loading (1-5 mol %) at room temperature in toluene. Appending a fluorous tag, as in 5a-c, simplifies the isolation procedure, while preserving high enantioselectivity (< or =92% ee).
Malkov
Andrei V
AV
Department of Chemistry, WestChem, Joseph Black Building, University of Glasgow, Glasgow G12 8QQ, Scotland, United Kingdom. amalkov@chem.gla.ac.uk
Figlus
Marek
M
Stoncius
Sigitas
S
Kocovský
Pavel
P
D000596:Amino Acids / Q000737:chemistry*; D002384:Catalysis; D005461:Fluorine / Q000737:chemistry*; D005559:Formamides / Q000737:chemistry*; D007097:Imines / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D012821:Silanes / Q000737:chemistry*
D000596:Amino Acids; D005559:Formamides; D007097:Imines; D012821:Silanes; D005461:Fluorine; C065893:trichlorosilane