Issue 50, 2014

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

Abstract

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).

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

Supplementary files

Article information

Article type
Communication
Submitted
02 Apr 2014
Accepted
01 May 2014
First published
06 May 2014
This article is Open Access
Creative Commons BY license

Chem. Commun., 2014,50, 6623-6625

Author version available

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

D. Scharnagel, F. Prause, J. Kaldun, R. G. Haase and M. Breuning, Chem. Commun., 2014, 50, 6623 DOI: 10.1039/C4CC02429J

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