Issue 25, 2018

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

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

Supplementary files

Article information

Article type
Paper
Submitted
16 apr 2018
Accepted
19 may 2018
First published
06 iyn 2018

Org. Biomol. Chem., 2018,16, 4675-4682

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, 16, 4675 DOI: 10.1039/C8OB00894A

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