Efficient kinetic resolution in the asymmetric hydrosilylation of imines of 3-substituted indanones and 4-substituted tetralones.
Kinetic resolution of the N-methyl imines of 3-substituted indanones and 4-substituted tetralones could be accomplished by hydrosilylation with a chiral titanocene catalyst. N-Methyl imines of 4-substituted tetralones were resolved to yield, after hydrolysis of the unreacted starting materials, ketones with high ee's and the amine products with high diastereomeric and enantiomeric purity. The utility of this process was demonstrated in the synthesis of sertraline.
Yun
J
J
Department of Chemistry, Massachusettes Institute of Technology, Cambridge, Massachusetts 02139, USA.
Buchwald
S L
SL
D007097:Imines / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D007700:Kinetics; D019158:N-Acetylneuraminic Acid / Q000737:chemistry*; D020280:Sertraline / Q000138:chemical synthesis; D013057:Spectrum Analysis; D013237:Stereoisomerism
D007097:Imines; D007659:Ketones; D019158:N-Acetylneuraminic Acid; D020280:Sertraline