Organocatalytic asymmetric conjugate addition of substituted 5-benzylfurfurals to nitroalkenes based on stereocontrol of trienamine

[Display omitted] •Diaminomethylenemalononitrile is good catalyst for asymmetric ε-alkylation reactions.•High stereoselectivity by a methyl group at γ-position of 5-benzylfurfural.•Higher stereoselectivities in comparison with the previous reports. Asymmetric ε-alkylation reaction of substituted 5-b...

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Veröffentlicht in:Tetrahedron letters 2020-02, Vol.61 (6), p.151478, Article 151478
Hauptverfasser: Akutsu, Hiroshi, Ito, Mifuyu, Kawada, Masahiro, Nakashima, Kosuke, Hirashima, Shin-ichi, Miura, Tsuyoshi
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Sprache:eng
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Zusammenfassung:[Display omitted] •Diaminomethylenemalononitrile is good catalyst for asymmetric ε-alkylation reactions.•High stereoselectivity by a methyl group at γ-position of 5-benzylfurfural.•Higher stereoselectivities in comparison with the previous reports. Asymmetric ε-alkylation reaction of substituted 5-benzylfurfural derivatives to nitroalkenes by controlling the stereochemistry of the trienamine intermediate resulted in corresponding ε-regioselective addition products in high yields, diastereoselectivities, and enantioselectivities.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2019.151478