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Synfacts 2022; 18(04): 0407
DOI: 10.1055/s-0041-1737384
Polymer-Supported Synthesis

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

Contributor(s):
Yasuhiro Uozumi
,
Aya Tazawa
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.
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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.


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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).


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Publication History

Article published online:
18 March 2022

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