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Synlett
DOI: 10.1055/a-2307-0645
letter

Tripeptide-Catalyzed Asymmetric Michael Addition Reaction of β-Nitrostyrenes with Cyclohexanone

Maeda Kippei
a   Graduate School of Manufacturing Engineering, Kitami Institute of Technology, 165 Koen-Cho, Kitami, Hokkaido 090-8507, Japan
,
Mitsuki Takeyama
a   Graduate School of Manufacturing Engineering, Kitami Institute of Technology, 165 Koen-Cho, Kitami, Hokkaido 090-8507, Japan
,
Yoshihito Kohari  ∗
b   School of Earth, Energy and Environmental Engineering, Faculty of Engineering, Kitami Institute of Technology, 165 Koen-Cho, Kitami, Hokkaido 090-8507, Japan
,
Miki Murata
a   Graduate School of Manufacturing Engineering, Kitami Institute of Technology, 165 Koen-Cho, Kitami, Hokkaido 090-8507, Japan
b   School of Earth, Energy and Environmental Engineering, Faculty of Engineering, Kitami Institute of Technology, 165 Koen-Cho, Kitami, Hokkaido 090-8507, Japan
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Abstract

A tripeptide catalyst derived from natural l-amino acids was employed in the reaction of β-nitrostyrenes with cyclohexanone, serving as a model for the asymmetric Michael addition reaction. The reaction was conducted in the presence of H-Pro-Tle-Gly-OH and 2-fluoro-4-chlorobenzoic acid as co-catalysts (each at 20 mol%) in DMF-H2O (5:1) at 0 °C for 3 days. This process yielded the desired Michael adducts with excellent efficiency and good stereoselectivity (up to 98% yield, up to 92% ee).

Key words

asymmetric synthesis - Michael addition - peptides - organocatalysts

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-2307-0645.
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Publication History

Received: 05 March 2024

Accepted after revision: 15 April 2024

Accepted Manuscript online:
15 April 2024

Article published online:
25 April 2024

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