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Catalytic asymmetric hydrogenation of pyrimidines.

Angew Chem Int Ed Engl

February 2015

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).

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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