(2S,5R)-2-Methylaminomethyl-1-methyl-5-phenylpyrrolidine, a chiral diamine ligand for copper(II)-catalysed Henry reactions with superb enantiocontrol

(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, hetero...

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Veröffentlicht in:Chemical communications (Cambridge, England) England), 2014-06, Vol.50 (50), p.6623-6625
Hauptverfasser: Scharnagel, Dagmar, Prause, Felix, Kaldun, Johannes, Haase, Robert G, Breuning, Matthias
Format: Artikel
Sprache:eng
Schlagworte:
Aldehydes
Aliphatic compounds
Diamines
Ligands
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Zusammenfassung: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).
ISSN:1359-7345
1364-548X
DOI:10.1039/c4cc02429j