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Exploiting Sm(II) and Sm(III) in SmI2-initiated reaction cascades: application in a tag removal-cyclisation approach to spirooxindole scaffolds

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  • Chemistry


SI_ChemSci_21_04_2011 S 1 Exploiting reagent evolution in samarium-mediated reaction cascades: application in a tag removal-cyclisation approach to spirooxindole scaffolds Susannah C. Coote, Seidjolo Quenum and David J. Procter* School of Chemistry, University of Manchester, Oxford Road, Manchester, M13 9PL, UK. Email: [email protected] Supporting Information Contents S 2 General experimental and general procedures S 9 Experimental: Synthesis of alkylated fluorous-tagged oxindoles S 29 Experimental: Synthesis of spirooxindoles S 47 Experimental: Recycling of the fluorous tag S 47 Experimental: Synthesis of analogues of spirotryprostatin A S 65 1H and 13C NMR spectra of new compounds S 118 X-ray crystal structures of spirooxindoles 19a, 19b, 23, 35 and 40b S 120 NOE study on diketopiperazines 39a and 39b S 121 References for the Supporting Information Electronic Supplementary Material (ESI) for Organic and Biomolecular Chemistry This journal is © The Royal Society of Chemistry 2011 S 2 General Experimental All experiments were performed under an atmosphere of nitrogen using anhydrous solvents, unless stated otherwise. Glassware for inert atmosphere reactions was oven- dried and cooled under a flow of nitrogen. THF was freshly distilled from sodium/benzophenone, CH2Cl2 and Et3N were freshly distilled from CaH2. Petroleum ether refers to the fraction of petroleum ether boiling in the range 40-60 ºC. All other solvents and reagents were purchased from commercial sources and used as supplied. Except where indicated otherwise, imines were prepared according to literature procedures. 1H NMR and 13C NMR spectra were recorded on a 400 MHz or 500 MHz spectrometer, with chemical shift values being reported in parts per million (ppm) relative to residual CHCl3 (δH = 7.27) and CDCl3 (δC = 77.0) as internal standards unless otherwise stated. All coupling constants

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