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
DOI:
10.1002/adsc.202101152
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).
