Asymmetric Transfer Hydrogenation of α-Keto Amides; Highly Enantioselective Formation of Malic Acid Diamides and α-Hydroxyamides

Gediya, Shweta K.; Vyas, Vijyesh K.; Clarkson, Guy J.; Wills, Martin

doi:10.1021/acs.orglett.1c02830

Cited by 5 publications

(2 citation statements)

References 52 publications

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“…The dataset we curated from the literature contained approximately 380 reactions. 1,14–34 This is not a very large dataset for ML. Currently, very popular deep learning algorithms cannot be applied in this work.…”

Section: Resultsmentioning

confidence: 99%

Prediction of the enantiomeric excess value for asymmetric transfer hydrogenation based on machine learning

Gao¹,

Chang²,

Tang

2023

Org. Chem. Front.

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Section: Resultsmentioning

confidence: 99%

Prediction of the enantiomeric excess value for asymmetric transfer hydrogenation based on machine learning

Gao¹,

Chang²,

Tang

2023

Org. Chem. Front.

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“…Tetramethylammonium hypochlorite (TMAOCl) was prepared by reacting an aqueous solution of tetramethylammonium hydroxide with chlorine gas. 19 Compounds 1a , 20 1b , 21 1c , 22 and 1f 23 were synthesized according to the reported methods, as were compounds 1d , 23 1e , 20 1g , 20 1h , 20 and 1i . 23…”

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confidence: 99%

Oxidative C–N Bond Cleavage of Cyclic Amines with Ammonium Hypochlorite

et al. 2023

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An oxidative C–N bond cleavage of cyclic amines has been developed under metal-free conditions, providing N-Cl-ω-amino acids in moderate to excellent yields. The reactions successfully proceed by using tetramethylammonium hypochlorite (TMAOCl) as an oxidant even on a gram scale. The Hofmann–Löffler–Freytag-type reaction of N-Cl-ω-amino acids to form cyclic amino acids are also demonstrated.

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Asymmetric Transfer Hydrogenation of Stable NH Imines for the Synthesis of Enantiopure α‐Chiral Primary Amines

Zhang,

Li,

et al. 2024

Chin. J. Chem.

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Comprehensive SummaryAlthough it offers a direct route to access synthetically valuable α‐chiral primary amines, asymmetric transfer hydrogenation of NH imines has been rarely studied, due in large part to the inaccessibility and instability of NH imines. Herein, we report a Rh‐catalyzed asymmetric transfer hydrogenation of a kind of novel and stable NH imines which are prepared via condensation of easily available sulfonylated 2’‐aminoacetophenones with NH3 in methanol. With this method, enantioenriched chiral 2‐(1‐aminoalkyl)anilines, which are privileged pharmacore groups, have been synthesized with good functional group compatibility, and with up to 99% ee. A gram‐scale reaction using 0.2 mol% of catalyst has been successfully performed to highlight the practicality. Furthermore, the products can be derivatized into enantiopure bioactive molecules as well as chiral tridentate ligands for metal catalysis.

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Asymmetric Transfer Hydrogenation of α-Keto Amides; Highly Enantioselective Formation of Malic Acid Diamides and α-Hydroxyamides

Cited by 5 publications

References 52 publications

Prediction of the enantiomeric excess value for asymmetric transfer hydrogenation based on machine learning

Prediction of the enantiomeric excess value for asymmetric transfer hydrogenation based on machine learning

Oxidative C–N Bond Cleavage of Cyclic Amines with Ammonium Hypochlorite

Asymmetric Transfer Hydrogenation of Stable NH Imines for the Synthesis of Enantiopure α‐Chiral Primary Amines

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