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.
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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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