Oxidative Functionalization of Aliphatic and Aromatic Amino Acid Derivatives with HO Catalyzed by a Nonheme Imine Based Iron Complex

Overview

Journal RSC Adv

Publisher Royal Society of Chemistry

Specialty Chemistry

Date 2022 May 11

PMID 35539690

Authors

Barbara Ticconi

Arianna Colcerasa

Stefano Di Stefano

Osvaldo Lanzalunga

Andrea Lapi

Marco Mazzonna

Giorgio Olivo

Affiliations

Soon will be listed here.

Abstract

The oxidation of a series of -acetyl amino acid methyl esters with HO catalyzed by a very simple iminopyridine iron(ii) complex 1 easily obtainable by self-assembly of 2-picolylaldehyde, 2-picolylamine, and Fe(OTf) was investigated. Oxidation of protected aliphatic amino acids occurs at the α-C-H bond exclusively (-AcAlaOMe) or in competition with the side-chain functionalization (-AcValOMe and -AcLeuOMe). -AcProOMe is smoothly and cleanly oxidized with high regioselectivity affording exclusively C-5 oxidation products. Remarkably, complex 1 is also able to catalyze the oxidation of the aromatic -AcPheOMe. A marked preference for the aromatic ring hydroxylation over Cα-H and benzylic C-H oxidation was observed, leading to the clean formation of tyrosine and its phenolic isomers.

Citing Articles

Increasing the steric hindrance around the catalytic core of a self-assembled imine-based non-heme iron catalyst for C-H oxidation.

Frateloreto F, Capocasa G, Olivo G, Abdel Hady K, Sappino C, Di Berto Mancini M RSC Adv. 2022; 11(1):537-542.

PMID: 35423066 PMC: 8690968. DOI: 10.1039/d0ra09677f.

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