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Helical-Peptide-Catalyzed Enantioselective Michael Addition Reactions and Their Mechanistic Insights

Atsushi Ueda*, Tomohiro Umeno, Mitsunobu Doi, Kengo Akagawa, Kazuaki Kudo and Masakazu Tanaka*

*Graduate School of Biomedical Sciences, Nagasaki University, 1-14 Bunkyo-machi, Nagasaki 852-8521, Japan, Email: auedanagasaki-u.ac.jp, matanakanagasaki-u.ac.jp

A. Ueda, T. Umeno, M. Doi, K. Akagawa, K. Kudo, M. Tanaka, J. Org. Chem., 2016, 81, 6343-6356.

DOI: 10.1021/acs.joc.6b00982 (free Supporting Information)


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Abstract

Helical peptide foldamers catalyze Michael addition reactions of nitroalkanes or dialkyl malonates to α,β-unsaturated ketones to give Michael adducts with high enantioselectivities. The amide protons at the N terminus in the α-helical peptide catalyst are crucial for activating Michael donors, while the N-terminal primary amine activates Michael acceptors through the formation of iminium ion intermediates.

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Key Words

nitro compounds, Michael Addition, organocatalysis


ID: J42-Y2016