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 5 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%

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