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
Format:	Artikel
Sprache:	eng
Schlagworte:	Alkylation Amino Acids - chemical synthesis Amino Acids - chemistry Catalysis Hydrocarbons - chemistry Molecular Structure Schiff Bases - chemistry Stereoisomerism
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creator	Ikeda, Tetsu Ochiishi, Haruka Yoshida, Mana Yazaki, Ryo Ohshima, Takashi
description	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.
doi_str_mv	10.1021/acs.orglett.1c04042
format	Article
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subjects	Alkylation Amino Acids - chemical synthesis Amino Acids - chemistry Catalysis Hydrocarbons - chemistry Molecular Structure Schiff Bases - chemistry Stereoisomerism
title	Catalytic Dehydrogenative β‑Alkylation of Amino Acid Schiff Bases with Hydrocarbon
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