ChemInform Abstract: Palladium‐Catalyzed Regioselective C‐5 Arylation of Protected L‐Histidine: Microwave‐Assisted C—H Activation Adjacent to Donor Arm.

Mahindra, Amit; Bagra, Nitin; Jain, Rahul

doi:10.1002/chin.201414140

Cited by 2 publications

(9 citation statements)

References 1 publication

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“…After flash column chromatography (petroleum ether/ethyl acetate = 8:2), compound 3h was obtained in 52% yield (40 mg) as yellow semisolid. 1 H NMR (500 MHz, DMSO-d 6 ): δ 8.91 (d, J = 7.8 Hz, 1H), 8.00 (d, J = 8.2 Hz, 1H), 7.96 (d,J = 8.6 Hz,2H), 7.54 (dd, J = 12.0, 7. 5 Hz,2H),1H), 7.44 (d, J = 6.9 Hz, 1H), 7.34 (d,J = 4.4 Hz,4H),7.27 (dd,J = 8.1,4.1 Hz,1H),4.68 (ddd,J = 10.2,8.0,5.7 Hz,1H),3.17 (dd,J = 13.8,5.4 Hz,1H),3.03 (dd,J = 13.7,10.3 Hz,1H), 1.44 (s, 9H).…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

“…1 H NMR (500 MHz, DMSO-d 6 ): δ 8.91 (d, J = 7.8 Hz, 1H), 8.00 (d, J = 8.2 Hz, 1H), 7.96 (d,J = 8.6 Hz,2H), 7.54 (dd, J = 12.0, 7. 5 Hz,2H),1H), 7.44 (d, J = 6.9 Hz, 1H), 7.34 (d,J = 4.4 Hz,4H),7.27 (dd,J = 8.1,4.1 Hz,1H),4.68 (ddd,J = 10.2,8.0,5.7 Hz,1H),3.17 (dd,J = 13.8,5.4 Hz,1H),3.03 (dd,J = 13.7,10.3 Hz,1H), 1.44 (s, 9H). 13 C{ 1 H} NMR (125 MHz, DMSO-d 6 ): δ 171.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

“…After flash column chromatography (petroleum ether/ethyl acetate = 8:2), compound 3m was obtained in 55% yield (44 mg) as brown semisolid. 1 H NMR (500 MHz, DMSO-d 6 ): δ 9.00 (d, J = 7.8 Hz, 1H), 8.00 (d, J = 8.1 Hz, 2H), 7.85 (d,J = 8.3 Hz,2H), 7.28 (q, J = 8.1 Hz, 4H), 7.19 (t, J = 6.8 Hz, 1H), 1H),3.11 (dt,J = 13.7,6.0 Hz,2H), 1.36 (s, 9H).…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

“…After flash column chromatography (petroleum ether/ethyl acetate = 8:2), compound 4a was obtained in 56% yield (32 mg) as yellow semisolid. 1 H NMR (500 MHz, ): δ 8.50 (d, J = 6.9 Hz, 1H), 7.87 (d,J = 8.6 Hz,2H), 7.00 (d,J = 8.7 Hz,2H),1H),3.81 (s,3H), 1.40 (s, 9H), 1.36 (d,J = 7.2 Hz,3H). 13 C{ 1 H} NMR (125 MHz, DMSO-d 6 ): δ 172.…”

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confidence: 99%

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Palladium-Catalyzed Aminocarbonylation of (Hetero)aryl Iodides with α-Amino Acid Esters as Nucleophiles

Rathod

Jain

2022

J. Org. Chem.

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We report palladium-catalyzed aminocarbonylation of (hetero)aryl iodides with α-amino acid esters as nucleophiles. The synthesized N-capped α-amino acids are biologically important building blocks. The mild conditions provide products with high enantioselectivity at 80 °C in 35 min. The reactions are performed under air in a sealed vessel using chloroform as an in situ CO source. For the first time, regioselective carbonylation of histidine is also presented.

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Section: ■ Experimental Sectionmentioning

confidence: 99%

Section: ■ Experimental Sectionmentioning

confidence: 99%

Section: ■ Experimental Sectionmentioning

confidence: 99%

mentioning

confidence: 99%

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Palladium-Catalyzed Aminocarbonylation of (Hetero)aryl Iodides with α-Amino Acid Esters as Nucleophiles

Rathod

Jain

2022

J. Org. Chem.

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“…We will also include the generation of nonaromatic products, if they are reported in the method, to communicate the entire scope of the presented entry. 236…”

Section: Synthesis Of Side Chain Fluorinated Aromatic Amino Acidsmentioning

confidence: 99%

Approaches to Obtaining Fluorinated α-Amino Acids

et al. 2019

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Fluorine does not belong to the pool of chemical elements that nature uses to build organic matter. However, chemists have exploited the unique properties of fluorine and produced countless fluoro-organic compounds without which our everyday lives would be unimaginable. The incorporation of fluorine into amino acids established a completely new class of amino acids and their properties, and those of the biopolymers constructed from them are extremely interesting. Increasing interest in this class of amino acids caused the demand for robust and stereoselective synthetic protocols that enable straightforward access to these building blocks. Herein, we present a comprehensive account of the literature in this field going back to 1995. We place special emphasis on a particular fluorination strategy. The four main sections describe fluorinated versions of alkyl, cyclic, aromatic amino acids, and also nickel-complexes to access them. We progress by one carbon unit increments. Special cases of amino acids for which there is no natural counterpart are described at the end of each section. Synthetic access to each of the amino acids is summarized in form of a table at the end of this article with the aim to make the information easily accessible to the reader.

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ChemInform Abstract: Palladium‐Catalyzed Regioselective C‐5 Arylation of Protected L‐Histidine: Microwave‐Assisted C—H Activation Adjacent to Donor Arm.

Cited by 2 publications

References 1 publication

Palladium-Catalyzed Aminocarbonylation of (Hetero)aryl Iodides with α-Amino Acid Esters as Nucleophiles

Palladium-Catalyzed Aminocarbonylation of (Hetero)aryl Iodides with α-Amino Acid Esters as Nucleophiles

Approaches to Obtaining Fluorinated α-Amino Acids

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