(2S,5R)-2-Methylaminomethyl-1-methyl-5-phenylpyrrolidine, a chiral diamine ligand for copper(II)-catalysed Henry reactions with superb enantiocontrol.
A cis-2-aminomethyl-5-phenylpyrrolidine, which is easily available from methyl Boc-L-pyroglutamate, was found to be a highly efficient chiral ligand for Cu(II)-catalysed Henry reactions. Excellent yields (>90%) and superb levels of enantiocontrol (98.5-99.6% ee) were reached with aromatic, heteroaromatic, vinylic, and aliphatic aldehydes (36 examples).
Organic Chemistry Laboratory, University of Bayreuth, Universitätsstraße 30, 95447 Bayreuth, Germany. matthias.breuning@uni-bayreuth.de.
Dagmar
D
Scharnagel
Felix
F
Prause
Johannes
J
Kaldun
Robert G
RG
Haase
Matthias
M
Breuning