Thio- and Seleno-Michael addition: An efficient tool for the delivery of sulfur and selenium functionalities

References

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• Some selected examples:
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• Typical procedure: Neutral Al2O3 (30 mg, 0.30 mmol, 3.0 eq.) was added under inert atmosphere (N2) to a stirred solution of the β-hydroxy thiol 1a [1-(allyloxy)-3-mercaptopropan-2-ol, R = CH2OAll] (0.10 mmol, 1.0 eq.) and methyl acrylate (0.12 mmol, 1.2 eq) in dry toluene (2 mL) at room temperature. The reaction mixture was stirred for 4 h, then diluted with Et2O (5 mL) and filtered through a short pad of Celite. Flash column chromatography (petroleum ether/Et2O 5:1) afforded methyl 3-[(3-(allyloxy)-2-hydroxypropyl)thio]propanoate 3a (R = CH2OAll) (16 mg, 64%) as a yellowish oil. 1H NMR (CDCl3, 400 MHz) δ (ppm): 2.42 (1H, bs, OH), 2.60-2.65 (3H, m), 2.71-2.85 (3H, m), 3.46 (1H, dd, J = 6.2 Hz, 9.6 Hz, CHaHbO), 3.52 (1H, dd, J = 4.2 Hz, 9.6 Hz; CHaHbO), 3.69 (3H, s), 3.87-3.93 (1H, CHOH), 4.01-4.03 (2H, m), 5.18-5.29 (2H, m), 5.84-5.94 (1H, m). 13C NMR (CDCl3, 100 MHz) δ (ppm): 27.5, 34.6, 35.9, 51.8, 69.4, 72.3, 72.6, 117.4, 134.4, 172.3. MS (ESI, positive), m/z (%): 234 (100, M+).
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• Tanini, D.; Tiberi, C.; Gellini, C.; Salvi, P. R.; Capperucci, A. A Straightforward Access to Stable β-Functionalized Alkyl Selenols. Adv. Synth. Catal. 2018, 360, 3367–3375. DOI:10.1002/adsc.201800602.
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