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Kuwano R, Hashiguchi Y, Ikeda R, et al. Catalytic asymmetric hydrogenation of pyrimidines. Angew Chem Int Ed Engl. 2015;54(8):2393-6doi: 10.1002/anie.201410607.
Kuwano, R., Hashiguchi, Y., Ikeda, R., & Ishizuka, K. (2015). Catalytic asymmetric hydrogenation of pyrimidines. Angewandte Chemie (International ed. in English), 54(8), 2393-6. https://doi.org/10.1002/anie.201410607
Kuwano, Ryoichi, et al. "Catalytic asymmetric hydrogenation of pyrimidines." Angewandte Chemie (International ed. in English) vol. 54,8 (2015): 2393-6. doi: https://doi.org/10.1002/anie.201410607
Kuwano R, Hashiguchi Y, Ikeda R, Ishizuka K. Catalytic asymmetric hydrogenation of pyrimidines. Angew Chem Int Ed Engl. 2015 Feb 16;54(8):2393-6. doi: 10.1002/anie.201410607. Epub 2015 Jan 07. PMID: 25565291.
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Angew Chem Int Ed Engl. 2015 Feb 16;54(8):2393-6. doi: 10.1002/anie.201410607. Epub 2015 Jan 07.

Catalytic asymmetric hydrogenation of pyrimidines.

Angewandte Chemie (International ed. in English)

Ryoichi Kuwano, Yuta Hashiguchi, Ryuhei Ikeda, Kentaro Ishizuka

Affiliations

  1. Department of Chemistry, Graduate School of Sciences, and International Research Center for Molecular Systems (IRCMS), Kyushu University, 6-10-1 Hakozaki, Higashi-ku, Fukuoka 812-8581 (Japan); JST ACT-C, 6-10-1 Hakozaki, Higashi-ku, Fukuoka 812-8581 (Japan). [email protected].

PMID: 25565291 DOI: 10.1002/anie.201410607

Abstract

The asymmetric hydrogenation of pyrimidines proceeded with high enantioselectivity (up to 99% ee) using an iridium catalyst composed of [IrCl(cod)]2, a ferrocene-containing chiral diphosphine ligand (Josiphos), iodine, and Yb(OTf)3 (cod = 1,5-cyclooctadiene). The chiral catalyst converted various 4-substituted pyrimidines into chiral 1,4,5,6-tetrahydropyrimidines in high yield. The lanthanide triflate is crucial for achieving the high enantioselectivity as well as for activating the heteroarene substrate.

© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Keywords: asymmetric catalysis; heterocycles; hydrogenation; iridium; lanthanides

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