Tandem catalysis in the polycyclisation of dienes to produce multi-substituted tetrahydrofurans

Tetrahedron Letters

Volumn 50, Issue 26, 2009, Pages 3523-3526

  Donohoe, Timothy J ^a   Lindsay Scott, Peter J ^a   Parker, Jeremy S ^b  

^a UNIVERSITY OF OXFORD   (United Kingdom)

^b ASTRAZENECA   (United Kingdom)

Author keywords

Osmium; Oxidation; Polycyclisation; Tandem catalysis

Indexed keywords

ALKADIENE; OSMIUM; OXAZOLIDINONE DERIVATIVE; TETRAHYDROFURAN DERIVATIVE;

ACIDITY; AMINOHYDROXYLATION; ARTICLE; CATALYSIS; CHEMICAL REACTION; CYCLIZATION; OXIDATION; PH; SYNTHESIS;

EID: 65649119011     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.03.027     Document Type: Article

References (21)

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16. General procedure 1: One-pot TA/oxidative cyclisation: potassium osmate dihydrate (0.01 equiv) was added to a solution of the hydroxamic ester (1 equiv) in a 3:1 mixture of acetonitrile-water (20 mL per mmol substrate) and the reaction mixture stirred at 50 °C for 2 h. (±)-Camphor-10-sulfonic acid (6 equiv), pyridine N-oxide (2 equiv) and citric acid (0.75 equiv) were added and the reaction mixture stirred at 50 °C for a further 16 h. The reaction was quenched by addition of solid sodium sulfite (10 mg), stirred for 30 min, washed with aqueous 2 M sodium hydroxide (5 mL) and extracted with ethyl acetate (3 × 5 mL). The combined organic extracts were dried over sodium sulfate, filtered and concentrated. The residue was dissolved in pyridine (1 mL) and acetic anhydride (1 mL) and the resultant mixture stirred at room temperature for 16 h. The reaction mixture was concentrated and the crude product purified by flash column chromatography. The beneficial effect of citric acid on osmium-catalysed processes has been documented; see Dupau, P.; Epple, R.; Thomas, A. A.; Fokin, V. V.; Sharpless, K. B. Adv. Synth. Catal. 2002, 344, 421.
17. + 280.1155, found 280.1155 (0.08 ppm).
18. Data were collected at low temperature using an Enraf-Nonius KCCD diffractometer [Otwinowski, Z.; Minor, W. Processing of X-ray Diffraction Data Collected in Oscillation Mode, In Methods Enzymol. Carter, C. W., Sweet, R. M., Eds.; Academic Press, 1997, Vol. 276.]. The Crystal structures were solved using SIR92 [Altomare, A.; Cascarano, G.; Giacovazzo, C.; Guagliardi, A.; Burla, M.C.; Polidori, G.; Camalli, M. J. Appl. Crystallogr. 1994, 27, 435.] and refined using the CRYSTALS software suite [Betteridge, P.W.; Carruthers, J.R.; Cooper, R.I.; Prout, K.; Watkin, D.J. J. Appl. Crystallogr. 2003, 36, 1487.], as per the CIF. Crystallographic data (excluding structure factors) for this compound have been deposited with the Cambridge Crystallographic Data Centre (CCDC 721466) and copies of these data can be obtained free of charge via www.ccdc.cam.ac.uk/data_request/cif.
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