1. Catalytic Asymmetric Hydrogenation of Pyrimidines
- Author
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Yuta Hashiguchi, Ryoichi Kuwano, Ryuhei Ikeda, and Kentaro Ishizuka
- Subjects
Lanthanide ,Chemistry ,Ligand ,Asymmetric hydrogenation ,Enantioselective synthesis ,chemistry.chemical_element ,General Medicine ,General Chemistry ,Medicinal chemistry ,Catalysis ,Yield (chemistry) ,Organic chemistry ,Iridium ,Trifluoromethanesulfonate - 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.
- Published
- 2015
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