A simple and efficient asymmetric hydrogenation of heteroaromatic ketones with iridium catalyst composed of chiral diamines and achiral phosphines

[Display omitted] •An Iridium catalyst was used for heteroaromatic ketones asymmetric hydrogenation;•Cheap phosphine ligands and cinchona alkaloids derivatives were used;•A series of heteroaromatic ketones has been well asymmetric hydrogenated;•98.6% ee and high up to 2.18 × 104(1/h) TOF were obtain...

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Veröffentlicht in:Tetrahedron letters 2020-09, Vol.61 (39), p.152356, Article 152356
Hauptverfasser: Li, Chun, Lu, Xunhua, Wang, Mengna, Zhang, Ling, Jiang, Jian, Yan, Shunfa, Yang, Yuanyong, Zhao, Yonglong, Zhang, Lin
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Sprache:eng
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Zusammenfassung:[Display omitted] •An Iridium catalyst was used for heteroaromatic ketones asymmetric hydrogenation;•Cheap phosphine ligands and cinchona alkaloids derivatives were used;•A series of heteroaromatic ketones has been well asymmetric hydrogenated;•98.6% ee and high up to 2.18 × 104(1/h) TOF were obtained under mild conditions. An efficient iridium catalyst composed of a simple and commercially available o-methoxytriphenylphosphine and 9-Amino (9-deoxy) epi-cinchonine was applied to the asymmetric hydrogenation of heteroaromatic ketones. A range of simple heteroaromatic ketones could be hydrogenated with good to excellent enantioselectivities and high activities. In particular, thiophene ketones and furyl ketones furnished 98.6% ee with up to 2.18 × 104(1/h) TOF. This catalytic system can be of practical value.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2020.152356