Cobalt-Catalyzed Efficient Asymmetric Hydrogenation of α-Primary Amino Ketones

Yang, Huiwen; Hu, Yanhua; Zou, Yashi; Zhang, Zhenfeng; Zhang, Wanbin

doi:10.1021/jacsau.3c00524

Cited by 10 publications

(5 citation statements)

References 47 publications

(67 reference statements)

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“…Another example of functional group-assisted activation on hydrogenation of the CO bond was reported in 2023 by Zhang et al But Ph-BPE was not the best ligand for that reaction due to its moderate yield (65%) and ee value (63%). 51…”

Section: Reactionsmentioning

confidence: 99%

Chiral bisphosphine Ph-BPE ligand: a rising star in asymmetric synthesis

Mei,

Ma,

Chen

et al. 2024

Chem. Soc. Rev.

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Section: Reactionsmentioning

confidence: 99%

Chiral bisphosphine Ph-BPE ligand: a rising star in asymmetric synthesis

Mei,

Ma,

Chen

et al. 2024

Chem. Soc. Rev.

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“…Very recently, Wanbin Zhang, Zhenfeng Zhang, and co-workers have realized an efficient Co-catalyzed asymmetric hydrogenation of α-primary amino ketones using BenzP* as the chiral ligand (Scheme ). The hydrogenation could be conducted on the gram scale with a low catalyst loading (up to 1000 S/C), delivering synthetically valuable vicinal alcohol units in excellent enantioselectivities. The mechanistic investigations suggested a nonredox cobalt(II) catalyst cycle and a proton shuttle activated outer-sphere reaction mode.…”

Section: Applications Of P-stereogenic Phosphorus Ligands In Asymmetr...mentioning

confidence: 99%

P-Stereogenic Phosphorus Ligands in Asymmetric Catalysis

Imamoto

2024

Chem. Rev.

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Chiral phosphorus ligands play a crucial role in asymmetric catalysis for the efficient synthesis of useful optically active compounds. They are largely categorized into two classes: backbone chirality ligands and P-stereogenic phosphorus ligands. Most of the reported ligands belong to the former class. Privileged ones such as BINAP and DuPhos are frequently employed in a wide range of catalytic asymmetric transformations. In contrast, the latter class of P-stereogenic phosphorus ligands has remained a small family for many years mainly because of their synthetic difficulty. The late 1990s saw the emergence of novel P-stereogenic phosphorus ligands with their superior enantioinduction ability in Rh-catalyzed asymmetric hydrogenation reactions. Since then, numerous P-stereogenic phosphorus ligands have been synthesized and used in catalytic asymmetric reactions. This Review summarizes P-stereogenic phosphorus ligands reported thus far, including their stereochemical and electronic properties that afford high to excellent enantioselectivities. Examples of reactions that use this class of ligands are described together with their applications in the construction of key intermediates for the synthesis of optically active natural products and therapeutic agents. The literature covered dates back to 1968 up until December 2023, centering on studies published in the late 1990s and later years.

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“…[95] Z. Zhang, W. Zhang and co-workers developed an efficient method for the synthesis of benzylic-β-aminoalcohols via asymmetric hydrogenation of protonated aromatic aminoketones using Co/(R,R)BenzP* as catalyst. [96] They proposed a specific substrate coordination mode through the amino group (À NH 2 ) assisted by H 2 CO 3 (Scheme 45), which is quite different from the conventional catalyst-substrate complex formation/activation via coordination of the hydroxy (À OH), amide, acid or ester groups (NHCOR, COOR, COOH) to the metal center in Co-catalyzed asymmetric hydrogenation. The catalytic activity was dramatically reduced by altering the carbon chain length between the NH 2 and the C=O group which confirmed the specific mode of catalyst/substrate activation.…”

Section: C=o Hydrogenationmentioning

confidence: 99%

“…Co/BenzP* catalyzed asymmetric hydrogenation of αprimary amino ketones. [96] Scheme 46. General scheme for cobalt-catalyzed asymmetric imine hydrogenation.…”

Section: C=n Hydrogenationmentioning

confidence: 99%

Cobalt‐Catalyzed Asymmetric Hydrogenation: Substrate Specificity and Mechanistic Variability

Chakrabortty,

de Bruin,

de Vries

2023

Angew Chem Int Ed

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Asymmetric hydrogenation finds widespread application in academia and industry. And indeed, a number of processes have been implemented for the production of pharma and agro intermediates as well as flavors & fragrances. Although these processes are all based on the use of late transition metals as catalysts, there is an increasing interest in the use of base metal catalysis in view of their lower cost and the expected different substrate scope. Catalysts based on cobalt have already shown their potential in enantioselective hydrogenation chemistry. This review outlines the impressive progress made in recent years on cobalt‐catalyzed asymmetric hydrogenation of different unsaturated substrates. We also illustrate the ligand dependent substrate specificity as well as the mechanistic variability in detail. This may well guide further catalyst development in this research area.

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Cobalt-Catalyzed Efficient Asymmetric Hydrogenation of α-Primary Amino Ketones

Cited by 10 publications

References 47 publications

Chiral bisphosphine Ph-BPE ligand: a rising star in asymmetric synthesis

Chiral bisphosphine Ph-BPE ligand: a rising star in asymmetric synthesis

P-Stereogenic Phosphorus Ligands in Asymmetric Catalysis

Cobalt‐Catalyzed Asymmetric Hydrogenation: Substrate Specificity and Mechanistic Variability

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