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Silver-catalyzed regioselective hydroamination of alkenyl diazoacetates to synthesize γ-amino acid equivalents

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Abstract

A simple protocol to directly access γ-amino acid derivatives by intermolecular regioselective hydroamination of trichloroethyl alkenyldiazoacetates with carbamate using a silver tetrafluoroborate catalyst is described. Density functional theory (DFT) calculations to analyze the reaction mechanism revealed that multiple attractive interactions occur in a transition state to promote the vinylogous addition of nitrogen nucleophiles.

Graphical abstract: Silver-catalyzed regioselective hydroamination of alkenyl diazoacetates to synthesize γ-amino acid equivalents

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Publication details

The article was received on 16 Apr 2018, accepted on 19 May 2018 and first published on 06 Jun 2018


Article type: Paper
DOI: 10.1039/C8OB00894A
Citation: Org. Biomol. Chem., 2018, Advance Article
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    Silver-catalyzed regioselective hydroamination of alkenyl diazoacetates to synthesize γ-amino acid equivalents

    J. Ueda, S. Harada, H. Nakayama and T. Nemoto, Org. Biomol. Chem., 2018, Advance Article , DOI: 10.1039/C8OB00894A

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