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Synlett 2019; 30(12): 1419-1426
DOI: 10.1055/s-0037-1611855
DOI: 10.1055/s-0037-1611855
letter
A Highly Efficient Magnetic Iron(III) Nanocatalyst for Ferrier Rearrangements
The project was supported by the Natural Science Foundation of Shanghai (11ZR1410400), large instruments Open Foundation of East China Normal University (20161043) and National Undergraduate Training Program for Innovation and Entrepreneurship (201710269030G).
Further Information
Publication History
Received: 03 April 2019
Accepted after revision: 15 May 2019
Publication Date:
19 June 2019 (online)
Abstract
A novel and highly efficient magnetic Fe3O4@C@Fe(III) core–shell catalyst, in which the carbon shell was prepared from lotus leaf, was fabricated. This nanocatalyst was successfully applied in the synthesis of a series of 2,3-unsaturated O-glycosides in excellent yields and with high selectivity, especially in the case of 2-halo O-glycosides, which differ in reactivity from nonsubstituted O-glycosides, but which have scarcely been explored before. Moreover, the catalyst could be easily separated from the reaction by the application of an external magnetic force and reused a minimum of five times without any significant decrease in the yields of the products. In addition, the reaction proceeded readily on a gram scale, which provides a bright prospect for future applications.
Key words
nanocatalyst - Ferrier rearrangement - haloglucals - iron catalysis - catalyst recycling - magnetic catalystSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1611855.
- Supporting Information
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- 61 Benzyl 4,6-Di-O-acetyl-2,3-dideoxy-α-d-erythro-hex-2-enopyranoside (3a); Typical Procedure Fe3O4@C@Fe(Ш) catalyst (8 mg, 0.01 mmol) was added to a mixture of 3,4,6-tri-O-acetyl-d-glucal (1a, 0.1 mmol, 27.2 mg) and BnOH (2a; 1.2 mmol, 12.5 ul) in CH2Cl2 (1.0 mL) and the mixture was stirred at rt (25 °C) under N2. On consumption of the glucal (TLC), the mixture and catalyst were separated magnetically. The solution was then evaporated to give a crude product that was purified by column chromatography [silica gel, PE–EtOAc (6:1)] to give a colorless oil; yield 29.8 mg. (93%). Benzyl 4,6-Di-O-diacetyl-2,3-dideoxyalpha-d-erythro-2-hexenopyranoside (3a) 1H NMR (500 MHz, CDCl3): δ = 7.36 (d, J = 4.9 Hz, 5 H), 5.90 (d, J = 10.4 Hz, 1 H), 5.87–5.83 (m, 1 H), 5.33 (dd, J = 9.4, 1.3 Hz, 1 H), 5.14 (s, 1 H), 4.81 (d, J = 11.7 Hz, 1 H), 4.60 (d, J = 11.7 Hz, 1 H), 4.25 (dd, J = 11.6, 5.0 Hz, 1 H), 4.18–4.14 (m, 1 H), 4.14–4.11 (m, 1 H), 2.10 (s, 3 H), 2.08 (s, 3 H). LRMS (ESI+): m/z [M + Na]+ calcd for C17H20NaO6: 343.12; found: 343.15 (5-Formyl-2-furyl)methyl 4,6-Di-O-acetyl-2,3-dideoxy-2-iodo-α-d-erythro-hex-2-enopyranoside (7h) Yellow oil; yield: 39.4 mg (85%). 1H NMR (500 MHz, CDCl3): δ = 9.63 (s, 1 H), 7.23 (d, J = 3.1 Hz, 1 H), 6.63 (d, J = 2.9 Hz, 1 H), 6.50 (s, 1 H), 5.31 (d, J = 8.6 Hz, 1 H), 5.10 (s, 1 H), 4.75 (ddd, J = 19.2, 13.5, 7.4 Hz, 2 H), 4.20 (ddd, J = 30.1, 16.3, 5.3 Hz, 3 H), 2.09 (d, J = 6.9 Hz, 6 H). 13C NMR (125 MHz, CDCl3): δ = 177.85, 170.79, 170.11, 157.15, 152.98, 138.61, 121.97, 112.01, 99.17, 73.08, 67.21, 66.84, 62.93, 62.55, 20.99, 20.92. HRMS (ESI+): m/z [M + Na]+ calcd for C16H17INaO6: 486.9866; found: 486.9860. Methyl 2,3,4-Tri-O-benzyl-6-O-(4,6-di-O-acetyl-2-bromo-2,3-dideoxy-α-d-erythro-hex-2-enopyranosyl)-α-d-glucopyranoside (9b) Yellow oil; yield: 65.6 mg (87%). 1H NMR (500 MHz, CDCl3): δ = 7.36–7.28 (m, 15 H), 6.19 (s, 1 H), 5.32 (d, J = 8.7 Hz, 1 H), 5.15 (s, 1 H), 4.97 (d, J = 10.8 Hz, 1 H), 4.92 (d, J = 11.1 Hz, 1 H), 4.84–4.77 (m, 2 H), 4.66 (dd, J = 11.2, 8.5 Hz, 2 H), 4.59 (d, J = 3.0 Hz, 1 H), 4.19 (dd, J = 12.3, 5.1 Hz, 1 H), 4.13 (d, J = 10.9 Hz, 2 H), 4.01 (t, J = 9.2 Hz, 1 H), 3.89–3.81 (m, 2 H), 3.76 (d, J = 10.6 Hz, 1 H), 3.66 (t, J = 9.4 Hz, 1 H), 3.53 (dd, J = 9.7, 2.9 Hz, 1 H), 3.37 (s, 3 H), 2.08 (s, 3 H), 2.04 (s, 3 H). 13C NMR (125 MHz, CDCl3): δ = 170.81, 170.17, 138.87, 138.47, 138.24, 129.74, 128.60, 128.57, 128.54, 128.30, 128.19, 128.08, 127.88, 127.77, 122.54, 98.17, 97.80, 82.06, 80.01, 77.75, 75.93, 75.17, 73.54, 70.92, 66.93, 66.85, 66.57, 62.53, 55.37, 53.57, 21.00, 20.87. HRMS (ESI+): m/z [M + Na]+ calcd for C38H43BrNaO11: 777.1887; found: 777.1881. Ethyl 4,6-Di-O-acetyl-2-chloro-2,3-dideoxy-α-d-erythro-hex-2-enopyranoside (11a) Yellow oil; yield: 26.0 mg (89%). 1H NMR (500 MHz, CDCl3): δ = 5.98 (s, 1 H), 5.35 (d, J = 9.3 Hz, 1 H), 4.91 (s, 1 H), 4.25–4.14 (m, 3 H), 3.84 (dq, J = 14.3, 7.1 Hz, 1 H), 3.70–3.61 (m, 1 H), 2.09 (s, 3 H), 2.07 (s, 3 H), 1.28 (t, J = 7.1 Hz, 3 H). 13C NMR (125 MHz, CDCl3): δ = 170.80, 170.22, 132.85, 125.48, 96.65, 66.82, 66.25, 65.25, 62.62, 20.99, 20.86, 15.26. HRMS (ESI+): m/z [M + Na]+ calcd for C12H17ClNaO6: 315.0612; found: 315.0606.