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

J Org Chem

Department of Chemistry and Biochemistry, School of Advanced Science and Engineering , Waseda University, 3-4-1 Okubo , Shinjuku, Tokyo 169-8555 , Japan.

Published: October 2019

An efficient method for the asymmetric synthesis of 4-imidazolidinones via an iodine-catalyzed intramolecular N-H/C(sp)-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(sp)-H bonds were aminated, and various functional groups were tolerated.

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http://dx.doi.org/10.1021/acs.joc.9b01154DOI Listing

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