Citation: Ruixue Liu, Xiaobing Ding, Qiwei Lang, Gen-Qiang Chen, Xumu Zhang. Enantioselective and divergent construction of chiral amino alcohols and oxazolidin-2-ones via Ir-f-phamidol-catalyzed dynamic kinetic asymmetric hydrogenation[J]. Chinese Chemical Letters, ;2025, 36(3): 110037. doi: 10.1016/j.cclet.2024.110037 shu

Enantioselective and divergent construction of chiral amino alcohols and oxazolidin-2-ones via Ir-f-phamidol-catalyzed dynamic kinetic asymmetric hydrogenation

Ruixue Liu ^a ,
Xiaobing Ding ^a ,
Qiwei Lang ^{a, *,} ,
Gen-Qiang Chen ^{a, b, *,} ,
Xumu Zhang ^{a, c, *,}

a.
Department of Chemistry, Medi-Pingshan and Shenzhen Grubbs Institute, Southern University of Science and Technology, Shenzhen 518000, China
b.
Academy for Advanced Interdisciplinary Studies, Southern University of Science and Technology, Shenzhen 518000, China
c.
Chemistry and Chemical Engineering Guangdong Laboratory, Shantou 515031, China

langqw@sustech.edu.cn

chengq@sustech.edu.cn

zhangxm@sustech.edu.cn

Received Date: 12 March 2024
Revised Date: 10 May 2024
Accepted Date: 21 May 2024
Available Online: 22 May 2024

Figures(5)

The dynamic kinetic resolution (DKR) process remains a highly efficacious approach for constructing chiral amino alcohols via the catalytic asymmetric hydrogenation of α-amino ketones. We report herein a highly efficient and enantioselective anti-selective dynamic kinetic asymmetric hydrogenation of α-amino ketones catalyzed by Ir-(S)-f-phamidol system, providing various chiral amino alcohols and chiral oxazolidin-2-ones divergently with high diastereo- and enantioselectivity (up to 99% yield, up to 99% ee and up to 99:1 dr). In addition, the reaction could be performed on the gram-scale, and the resulting chiral amino alcohols are key intermediates of norephedrine and metaraminol.
- Asymmetric hydrogenation,
- α-Amino ketone,
- f-Phamidol,
- Iridium-catalysed,
- Divergent synthesis
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