Polymer-Supported Helical Peptide Catalyst for Enantioselective Nitro-Michael Addition

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).

Publication History

Article published online:
18 March 2022