Synthetic Utility of Sugar-Derived Cyclic Nitrones: A Diastereoselective Synthesis of Linear 4-Azatriquinanes

Abstract

A diastereoselective Pauson–Khand reaction has been utilized as the key step in the construction of azatriquinanes from sugar-derived nitrones.

Key words

diastereoselectivity - sugar derivatives - nitrones - ­Pauson–Khand reaction

• References and Notes

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• 14 Genaral Procedure for Pauson–Khand Reaction: To a stirred solution of enyne (1 mmol) in CH₂Cl₂ (30 mL), [Co₂(CO)₈] (1.2 mmol) was added under a nitrogen atmosphere at 25 °C. After stirring at 25 °C for 1 h, the solvent was removed to obtain the crude product. To a solution of the above crude product in toluene (20 mL), DMSO (10 mmol) was added and the solution was heated at reflux overnight at 80 °C. After completion, the reaction mixture was quenched with 1% HCl (50 mL) (except for compounds 33 and 34, which were quenched with water) and extracted with CH₂Cl₂. The combined organic layers were dried (Na₂SO₄) and concentrated. The crude product was purified by basic alumina column chromatography. Data for (1S,2S,3S,8aS,8bS)-1,2-bis(benzyloxy)-3-(benzyloxymethyl)-1,2,3,8,8a,8b-hexahydrocyclo-penta[a]pyrrolizin-7(5H)-one (15): R _f  = 0.4 (EtOAc–hexanes, 50%); [α] _d ²⁰ –9.8 (c 1.00, CHCl₃); ¹H NMR (CDCl₃, 400 MHz): δ = 7.37–7.26 (m, 15 H), 6.0–5.99 (m, 1 H), 4.69–4.44 (m, 6 H), 4.08–4.02 (m, 3 H), 3.71 (d, J = 16.9 Hz, 1 H), 3.62 (dd, J = 9.4, 4.5 Hz, 1 H), 3.52 (dd, J = 9.4, 6.5 Hz, 1 H), 3.29–3.24 (m, 1 H), 3.19 (dd, J = 10.5, 3.3 Hz, 1 H), 3.12–3.08 (m, 1 H), 2.60 (dd, J = 17.6, 6.2 Hz, 1 H), 2.10 (dd, J = 17.6, 3.3 Hz, 1 H); ¹³C NMR (100 MHz, CDCl₃): δ = 209.3, 186.9, 138.4, 138.1, 137.7, 128.7, 128.6, 128.5, 128.1, 128.0, 127.9, 127.8, 125.1, 86.8, 86.1, 73.6, 73.0, 72.7, 72.5, 72.3, 70.2, 54.2, 48.5, 40.6; IR (neat): 3872, 3030, 2924, 2854, 2109, 1966, 1703, 1646, 1454, 1367, 1306, 1215, 1106, 1028, 754, 698 cm^–1; HRMS (ESI): calcd for C₃₂H₃₄NO₄ [M + 1]⁺ 496.2488; found 496.2469