Enantioselective metal-free reduction of ketones by a user-friendly silane with a reusable chiral additive

Varjosaari, Sami E.; Skrypai, Vladislav; Herlugson, Sharon; Gilbert, Thomas M.; Adler, Marc J.

doi:10.1016/j.tetlet.2018.06.032

Cited by 7 publications

(8 citation statements)

References 35 publications

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“…FTIR (KBr): 3388, 2923, 2851, 1450, 1015, 759, 700, 578 cm –1 . Analytical data are in accordance with literature data. , …”

Section: Experimental Sectionsupporting

confidence: 86%

“…FTIR (KBr): 3335, 2944, 2829, 1608, 1558, 1456, 1395, 1285, 1274, 1149, 1110, 997, 811, 740, 696 cm –1 . Analytical data are in accordance with literature data …”

Section: Experimental Sectionsupporting

confidence: 85%

“…FTIR (KBr): 3195, 2987, 2933, 2863, 1498, 1436, 1270, 1065, 1035, 962, 911, 772, 737 cm –1 . Analytical data are in accordance with literature data …”

Section: Experimental Sectionsupporting

confidence: 85%

“…Analytical data are in accordance with literature data. 14 1-(p-Tolyl)ethan-1-ol (2l). The product (65.4 mg, 96% yield) was isolated using flash chromatography (15% EtOAc/DCM), as a yellow oil.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

“…1 H NMR (400 MHz, CDCl 3 ): δ 7.47−7.38 (m, 1H), 7.25−7.16 (m, 2H), 7.14−7.07 (m, 1H), 4.78 (q, J = 5.6, 3.8 Hz, 1H), 2.84−2.80 (m, 1H), 2.78−2.68 (m, 1H), 2.02−1.89 (m, 3H), 1.85−1.75 (m, 2H). 13 14 1-Phenylethane-1,2-diol (2u). The product (42.9 mg, 62% yield) was isolated using flash chromatography (50% EtOAc/PE), as a yellow solid.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

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A General Method for Photocatalytic Decarboxylative Hydroxylation of Carboxylic Acids

Khan

Zaman

et al. 2020

J. Org. Chem.

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A general and practical method for decarboxylative hydroxylation of carboxylic acids was developed through visible light-induced photocatalysis using molecular oxygen as the green oxidant. The addition of NaBH4 to in situ reduce the unstable peroxyl radical intermediate much broadened the substrate scope. Different sp3 carbon-bearing carboxylic acids were successfully employed as substrates, including phenylacetic acid-type substrates, as well as aliphatic carboxylic acids. This transformation worked smoothly on primary, secondary, and tertiary carboxylic acids.

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“…FTIR (KBr): 3388, 2923, 2851, 1450, 1015, 759, 700, 578 cm –1 . Analytical data are in accordance with literature data. , …”

Section: Experimental Sectionsupporting

confidence: 86%

“…FTIR (KBr): 3335, 2944, 2829, 1608, 1558, 1456, 1395, 1285, 1274, 1149, 1110, 997, 811, 740, 696 cm –1 . Analytical data are in accordance with literature data …”

Section: Experimental Sectionsupporting

confidence: 85%

“…FTIR (KBr): 3195, 2987, 2933, 2863, 1498, 1436, 1270, 1065, 1035, 962, 911, 772, 737 cm –1 . Analytical data are in accordance with literature data …”

Section: Experimental Sectionsupporting

confidence: 85%

Section: ■ Experimental Sectionmentioning

confidence: 99%

Section: ■ Experimental Sectionmentioning

confidence: 99%

See 3 more Smart Citations

A General Method for Photocatalytic Decarboxylative Hydroxylation of Carboxylic Acids

Khan

Zaman

et al. 2020

J. Org. Chem.

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Oxidation and Reduction

Banerji

2021

Organic Reaction Mechanisms Series

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Homobimetallic Ruthenium(II) Complexes Catalysed Selective Transfer Hydrogenation of Aldehydes in Water

Deshmukh,

Rana,

Rajaraman

et al. 2024

Chemistry An Asian Journal

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Herein we report chemoselective transfer hydrogenation (TH) of aldehydes in aqueous medium using a series of homobimetallic Ru(II) catalysts. Two homobimetallic complexes (Ru1 and Ru3) and one monometallic complex (Ru2) have been employed in the catalytic reduction of aldehydes. Bimetallic complex [(p‐cymene)2(RuCl)2L3] (Ru3) is obtained from the reaction of Schiff base ligand 2,2'‐((1E,1'E)‐((3,3',5,5'‐tetraisopropyl‐[1,1'‐biphenyl]‐4,4'diyl)bis(azaneylylidene))bis(methaneylylidene))bis(4‐bromophenol) (H2L3) and characterized by various spectroscopic and analytical techniques. The use of formic acid/formate buffer as the hydride source and a catalyst loading of 0.01 mol% of Ru1 or Ru3 resulted in the conversion of various aldehydes to the corresponding alcohols in good to excellent yield. This method is very efficient for selective reduction of aldehydes in the presence of other reducible functional groups. A loading of 0.0001 mol% of Ru1 catalyst is sufficient to achieve a turnover frequency (TOF) of 5.5× 105 h‐1. Furthermore, the catalyst can been recycled and reused for six consecutives cycles without sacrificing the efficiency. A comparison of results obtained between bimetallic and monometallic complexes offers valuable insights into the distinct reactivity patterns of the bimetallic complexes, presumably originating from a cooperative effect. We have explored the mechanistic pathway using DFT methods.

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Enantioselective metal-free reduction of ketones by a user-friendly silane with a reusable chiral additive

Cited by 7 publications

References 35 publications

A General Method for Photocatalytic Decarboxylative Hydroxylation of Carboxylic Acids

A General Method for Photocatalytic Decarboxylative Hydroxylation of Carboxylic Acids

Oxidation and Reduction

Homobimetallic Ruthenium(II) Complexes Catalysed Selective Transfer Hydrogenation of Aldehydes in Water

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