Catalytic Asymmetric Hydrogenation of Pyrimidines |
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| Authors: | Prof Ryoichi Kuwano Yuta Hashiguchi Ryuhei Ikeda Dr Kentaro Ishizuka |
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| Institution: | 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);2. JST ACT‐C, 6‐10‐1 Hakozaki, Higashi‐ku, Fukuoka 812‐8581 (Japan);3. Education Center for Global Leaders in Molecular Systems for Devices, Kyushu University, 774 Motooka, Nishi‐ku, Fukuoka, 819‐0395 (Japan) |
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| 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. |
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| Keywords: | asymmetric catalysis heterocycles hydrogenation iridium lanthanides |
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