Catalytic Dehydrogenative β‑Alkylation of Amino Acid Schiff Bases with Hydrocarbon

A synthetic method for the synthesis of a highly congested α,β-dehydroamino acid through the β-C–H bond activation of an amino acid Schiff base is described. Abundant hydrocarbon feedstock could be used as an alkylating reagent to afford an α,β-dehydroamino acid bearing a quaternary carbon at the γ-...

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Veröffentlicht in:Organic letters 2022-01, Vol.24 (1), p.369-373
Hauptverfasser: Ikeda, Tetsu, Ochiishi, Haruka, Yoshida, Mana, Yazaki, Ryo, Ohshima, Takashi
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Sprache:eng
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Zusammenfassung:A synthetic method for the synthesis of a highly congested α,β-dehydroamino acid through the β-C–H bond activation of an amino acid Schiff base is described. Abundant hydrocarbon feedstock could be used as an alkylating reagent to afford an α,β-dehydroamino acid bearing a quaternary carbon at the γ-position with an exclusively (Z)-geometry. Notably, a tetrasubstituted olefin could be constructed from saturated starting materials. The transformation of the synthesized α,β-dehydroamino acid into unnatural α-amino acid derivatives was also demonstrated.
ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.1c04042