Combined Computational and Experimental Studies on the Asymmetric Michael Addition of α‑Aminomaleimides to β‑Nitrostyrenes Using an Organocatalyst Derived from Cinchona Alkaloid
Maleimides are often used as electrophiles in conventional reactions; however, their application as nucleophiles is limited to only a few reactions, and reactions utilizing α-aminomaleimides as asymmetric Michael donors have not been reported to date. Thus, in this work, asymmetric Michael addition...
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| Veröffentlicht in: | Organic letters 2021-08, Vol.23 (15), p.5714-5718 |
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| container_title | Organic letters |
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| creator | Sakai, Naoki Kawashima, Kyohei Kajitani, Masashi Mori, Seiji Oriyama, Takeshi |
| description | Maleimides are often used as electrophiles in conventional reactions; however, their application as nucleophiles is limited to only a few reactions, and reactions utilizing α-aminomaleimides as asymmetric Michael donors have not been reported to date. Thus, in this work, asymmetric Michael addition of α-aminomaleimides as Michael donors to β-nitrostyrenes was conducted for the first time using an organocatalyst derived from a Cinchona alkaloid. Density functional theory investigations were crucial to improve the enantioselectivity of the adduct. |
| doi_str_mv | 10.1021/acs.orglett.1c01831 |
| format | Article |
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| title | Combined Computational and Experimental Studies on the Asymmetric Michael Addition of α‑Aminomaleimides to β‑Nitrostyrenes Using an Organocatalyst Derived from Cinchona Alkaloid |
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