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 |
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Hauptverfasser: | , , , , |
Format: | Artikel |
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. |
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ISSN: | 1523-7060 1523-7052 1523-7052 |
DOI: | 10.1021/acs.orglett.1c04042 |