Iodine-Catalyzed Synthesis of Chiral 4-Imidazolidinones Using α-Amino Acid Derivatives via Dehydrogenative N-H/C(sp3)-H Coupling

Stephen Kyalo Kanyiva, Marina Tane, Takanori Shibata

Research output: Contribution to journal › Article

2 Citations (Scopus)

Abstract

An efficient method for the asymmetric synthesis of 4-imidazolidinones via an iodine-catalyzed intramolecular N-H/C(sp3)-H activation of readily available and abundant feedstocks, amino acids, and amines is described. The reaction proceeded under visible light irradiation to afford a variety of 4-imidazolidinone derivatives under mild conditions in moderate to excellent yields. Secondary and tertiary C(sp3)-H bonds were aminated, and various functional groups were tolerated.

Original languageEnglish
JournalJournal of Organic Chemistry
DOIs
Publication statusAccepted/In press - 2019 Jan 1

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Iodine
Feedstocks
Functional groups
Amines
Chemical activation
Irradiation
Derivatives
Amino Acids

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Iodine-Catalyzed Synthesis of Chiral 4-Imidazolidinones Using α-Amino Acid Derivatives via Dehydrogenative N-H/C(sp3)-H Coupling. / Kanyiva, Stephen Kyalo; Tane, Marina; Shibata, Takanori.

In: Journal of Organic Chemistry, 01.01.2019.

Research output: Contribution to journal › Article

Kanyiva, SK, Tane, M & Shibata, T 2019, 'Iodine-Catalyzed Synthesis of Chiral 4-Imidazolidinones Using α-Amino Acid Derivatives via Dehydrogenative N-H/C(sp3)-H Coupling', Journal of Organic Chemistry. https://doi.org/10.1021/acs.joc.9b01154
Kanyiva SK, Tane M, Shibata T. Iodine-Catalyzed Synthesis of Chiral 4-Imidazolidinones Using α-Amino Acid Derivatives via Dehydrogenative N-H/C(sp3)-H Coupling. Journal of Organic Chemistry. 2019 Jan 1. https://doi.org/10.1021/acs.joc.9b01154
Kanyiva, Stephen Kyalo ; Tane, Marina ; Shibata, Takanori. / Iodine-Catalyzed Synthesis of Chiral 4-Imidazolidinones Using α-Amino Acid Derivatives via Dehydrogenative N-H/C(sp3)-H Coupling. In: Journal of Organic Chemistry. 2019.
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