Facile Reduction of Carboxylic Acids, Esters, Acid Chlorides, Amides and Nitriles to Alcohols or Amines Using NaBH4/BF3×Et2O.

Cho, Su‐Dong; Park, Yong‐Dae; Kim, Jeum‐Jong; Falck, John R.; Yoon, Yong‐Jin

doi:10.1002/chin.200434044

Cited by 5 publications

(7 citation statements)

References 13 publications

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“…Synthetic procedures and characterization details for all compounds can be found in the Supplementary Materials (Figures S1-S13). Spectral data of synthesized compounds are consistent with the literature [24][25][26][27][28][29][30][31][32][33][34][35][36][37][38][39].…”

Section: Computational Detailssupporting

confidence: 87%

The Reduction of Carbonyl Compounds with Dicyclopentylzinc: A New Example of Asymmetric Amplifying Autocatalysis

Saigitbatalova,

Latypova,

Zagidullin

et al. 2023

IJMS

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A previously unknown reduction of carbonyl compounds with dicyclopentylzinc is reported. Aldehydes react in mild conditions yielding corresponding primary alcohols and cyclopentene. Although cyclohexanone and acetophenone are inert to dicyclopentylzinc, a variety of heterocyclic ketones reacted readily, yielding reasonable to high yields of corresponding secondary alcohols. When the reaction was catalyzed with (–)-(1R,2S)-ephedrine, 3-acetylpyridine (10) resulted in a high yield of (S)-1-(pyridin-3-yl)ethanol (19) with >99% ee. 5-Acetyl-2-bromopyridine (11) also provided the corresponding optically active alcohol 20, albeit with a much lower optical yield. When 10% of 19 with 92% ee was used as an autocatalyst, 55% yield of the same compound was obtained, with 95% ee and 96% ee in two independent experiments. A three-stage reaction sequence starting from “no chirality” reaction yielded 19 with 6% ee. Thus, amplifying autocatalysis was detected in the reaction of ketone 10 with dicylopentylzinc.

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Section: Computational Detailssupporting

confidence: 87%

The Reduction of Carbonyl Compounds with Dicyclopentylzinc: A New Example of Asymmetric Amplifying Autocatalysis

Saigitbatalova,

Latypova,

Zagidullin

et al. 2023

IJMS

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“…For aldehydes 8 and 9, the carboxylic acid of 3 was selectively reduced using a mixture of sodium borohydride and boron trifluoride diethyl etherate. 35 The resulting alcohol (7) was oxidized using PDC to yield the corresponding aldehyde (8). Following hydrolysis of the methyl ester in 8 and subsequent conversion to the tert-butyl ester, aldehyde 9 was obtained.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Bisubstrate Inhibitors of Nicotinamide N-Methyltransferase (NNMT) with Enhanced Activity

Gao

Haren

Moret³

et al. 2019

J. Med. Chem.

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Nicotinamide N -methyltransferase (NNMT) catalyzes the methylation of nicotinamide to form N -methylnicotinamide. Overexpression of NNMT is associated with a variety of diseases, including a number of cancers and metabolic disorders, suggesting a role for NNMT as a potential therapeutic target. By structural modification of a lead NNMT inhibitor previously developed in our group, we prepared a diverse library of inhibitors to probe the different regions of the enzyme’s active site. This investigation revealed that incorporation of a naphthalene moiety, intended to bind the hydrophobic nicotinamide binding pocket via π–π stacking interactions, significantly increases the activity of bisubstrate-like NNMT inhibitors (half-maximal inhibitory concentration 1.41 μM). These findings are further supported by isothermal titration calorimetry binding assays as well as modeling studies. The most active NNMT inhibitor identified in the present study demonstrated a dose-dependent inhibitory effect on the cell proliferation of the HSC-2 human oral cancer cell line.

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“…It was proven that the reducing effect of added antioxidants, as well as naturally occurring redox substances of fruit juices, purée, milk, and yogurts, should be taken into account when evaluating the chemical safety of products containing benzoates. , Indeed, reduction conversions of benzoates to benzyl alcohol and to the more reduced substance (toluene) are thermodynamically possible and are in accordance with the reference data. ,− It was shown in practice, using GC-MS, that ascorbic acid reduces benzoic acid to toluene in the model system . However, the presence of catechins in apple juice affects the reducing power of ascorbic acid, therefore toluene was not found in apple juice containing benzoates .…”

Section: Redox Interactions In Foodstuffsmentioning

confidence: 88%

Electrochemical Basis for Re-evaluating Antioxidant Effect of Redox Substances in Foodstuffs

Bocharova

2022

ACS Food Sci. Technol.

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Differences in the mechanisms of in vitro antioxidant actions provide difficulties in evaluating antioxidant power and in choosing correct antioxidants for certain foodstuffs. In view of the reducing, antiradical, and pro-oxidant abilities of certain redox substances, an electrochemical approach was applied in this Review for re-evaluating antioxidant properties. The redox basis was discussed to provide a holistic view with respect to polyphenols acting both as reducing and antiradical agents. Quantitative (quantity of reduced forms) and qualitative (standard redox potential) constituents of reducing power were analyzed. Antioxidant vs pro-oxidant effects of polyphenols in foodstuffs were shown to rely upon the thermodynamic viability of redox reactions. It was demonstrated that the intermediate products of redox reactions of polyphenols (semiquinones) may act as antiradical agents. The article is based on previous works and outlines the further research for a practical application of electrical current in determining and improving the antioxidant capacity of foodstuffs.

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Facile Reduction of Carboxylic Acids, Esters, Acid Chlorides, Amides and Nitriles to Alcohols or Amines Using NaBH₄/BF₃×Et₂O.

Cited by 5 publications

References 13 publications

The Reduction of Carbonyl Compounds with Dicyclopentylzinc: A New Example of Asymmetric Amplifying Autocatalysis

The Reduction of Carbonyl Compounds with Dicyclopentylzinc: A New Example of Asymmetric Amplifying Autocatalysis

Bisubstrate Inhibitors of Nicotinamide N-Methyltransferase (NNMT) with Enhanced Activity

Electrochemical Basis for Re-evaluating Antioxidant Effect of Redox Substances in Foodstuffs

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