Tamaribuchi K,
Tian J,
Akagawa K,
Kudo K.
*
The University of Tokyo, Japan
Enantioselective Nitro-Michael Addition Catalyzed by N-Terminal Guanidinylated Helical Peptide.
Adv. Synth. Catal. 2022;
364: 82-86
Key words
asymmetric catalysis - nitro-Michael addition - peptide catalysis
Significance
An N-terminal guanidinylated helical peptide supported on PS-PEG resin 1 catalyzed the enantioselective nitro-Michael addition of acetylacetones or β-keto esters to nitroalkenes to afford the corresponding nitro-Michael adducts in up to 99% yield and 99% ee.
Comment
In the enantioselective nitro-Michael addition of acetylacetone to β-nitrostyrene, the catalyst was recovered and reused four times without loss of its catalytic performance. The authors have previously reported the synthesis of PS-PEG-supported peptide catalysts and their application in a cyanosilylation of aldehydes (Tetrahedron Lett.
2012, 53, 5981) and an enantioselective Michael addition (J. Org. Chem.
2016, 81, 6343).
