What is it about?
Enantioselective Henry reactions (nitro Aldol reactions) permit a fast access to chiral ß-nitro alcohols, which are versatile chiral building blocks for organic synthesis. We developed novel diamine, namely (2S,5R)-2-Methylaminomethyl-1-methyl-5-phenylpyrrolidine, that is 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.
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Why is it important?
There are quite a number of efficient chiral ligands for enantioselective, Cu(II)-catalysed Henry reactions known, but our ligand is the only one that permits superb levels of enantiocontrol (98.5–99.6% ee) with a wide variety of aromatic, heteroaromatic, vinylic, and aliphatic aldehydes (36 examples). Furthermore, it can be prepared in just a few steps from cheap methyl Boc-L-pyroglutamate.
Perspectives
I hope this chiral ligand will find many applications in the enantioselective synthesis of natural products, bioactive drugs, and chiral building blocks.
Professor Matthias Breuning
University of Bayreuth, Organic Chemistry Laboratory
Read the Original
This page is a summary of: (2S,5R)-2-Methylaminomethyl-1-methyl-5-phenylpyrrolidine, a chiral diamine ligand for copper(ii)-catalysed Henry reactions with superb enantiocontrol, Chemical Communications, January 2014, Royal Society of Chemistry,
DOI: 10.1039/c4cc02429j.
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