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Volumn 65, Issue 52, 2009, Pages 10882-10892

Corrigendum to "Manganese(III)-mediated oxidative free-radical cyclisations of allenyl malonates" [Tetrahedron 65 (2009) 10882-10892] (DOI:10.1016/j.tet.2009.09.112);Manganese(III)-mediated oxidative free-radical cyclisations of allenyl malonates

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID DERIVATIVE; ALKENYL GROUP; ALLENE DERIVATIVE; ALLYL COMPOUND; BICYCLO COMPOUND; FREE RADICAL; GAMMA LACTONE DERIVATIVE; MALONIC ACID DERIVATIVE; MANGANESE; SILANE DERIVATIVE;

EID: 70449702202     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2010.02.016     Document Type: Erratum
Times cited : (20)

References (46)
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    • For the synthesis of γ-lactones using
    • For the synthesis of γ-lactones using:
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    • manganese(III) acetate and copper(II) acetate see:
    • manganese(III) acetate and copper(II) acetate see:. Snider B.B., and McCarthy B.A. J. Org. Chem. 58 (1993) 6217-6223
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    • For reviews of the use of manganese(III) acetate in organic synthesis see
    • For reviews of the use of manganese(III) acetate in organic synthesis see:
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    • The stereochemical outcome of this reaction is in accord with the Beckwith-Houk model for the 5-exo-trig cyclisation of 5-hexenyl radicals see:
    • The stereochemical outcome of this reaction is in accord with the Beckwith-Houk model for the 5-exo-trig cyclisation of 5-hexenyl radicals see:. Beckwith A.L.J. Tetrahedron 37 (1981) 3073-3100
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    • For precedent for the formation of [3.3.0]-bicyclic γ-lactones by iodocyclisation of a cyclopentylmalonate onto a terminal alkene see:
    • For precedent for the formation of [3.3.0]-bicyclic γ-lactones by iodocyclisation of a cyclopentylmalonate onto a terminal alkene see:. Bian J.W., Van Wingerden M., and Ready J.M. J. Am. Chem. Soc. 128 (2006) 7428-7429
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    • It has previously been reported that exposure of β-dicarbonyl and related compounds to allylsilanes and manganese(III) acetates provides products in which the silyl group is retained, see:
    • It has previously been reported that exposure of β-dicarbonyl and related compounds to allylsilanes and manganese(III) acetates provides products in which the silyl group is retained, see:. Warsinsky R., and Steckhan E. J. Chem. Soc., Perkin Trans. 1 (1994) 2027-2037
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    • For the reduction of vinyl radicals with ethanol in the presence of manganese(III) acetate see: Ref 2a and
    • For the reduction of vinyl radicals with ethanol in the presence of manganese(III) acetate see: Ref 2a and. Snider B.B., Merritt J.E., Dombroski M.A., and Buckman B.O. J. Org. Chem. 56 (1991) 5544-5553
    • (1991) J. Org. Chem. , vol.56 , pp. 5544-5553
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    • For the use of copper(II) triflate in conjunction with manganese(III) acetate see: Refs 1, 7 and 14
    • For the use of copper(II) triflate in conjunction with manganese(III) acetate see:. Toyao A., Chikaoka S., Takeda Y., Tamura O., Muraoka O., Tanabe G., and Ishibashi H. Tetrahedron Lett. 42 (2001) 1729-1732 Refs 1, 7 and 14
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    • note
    • The connectivity was confirmed by COSY and HSQC experiments.
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    • note
    • Treatment of the allene 25 with manganese(III) acetate in acetonitrile with no copper(II) salt, gave a whole myriad of products including the dimers 37, the acetates 39 and 41, and the diols 40 and 42.
  • 30
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    • note
    • -1) and the connectivity was confirmed by COSY and HSQC experiments.
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    • The structure was determined from single crystal X-ray diffraction data collected at low temperature with an Oxford Cryosystems Cryostream N2 open-flow cooling device [Ref: ]
    • The structure was determined from single crystal X-ray diffraction data collected at low temperature with an Oxford Cryosystems Cryostream N2 open-flow cooling device [Ref:. Cosier J., and Glazer A.M. J. Appl. Crystallogr. 19 (1986) 105-107 ]
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    • Processing of X-ray Diffraction Data Collected in Oscillation Mode
    • Data were collected using an Enraf-Nonius KappaCCD diffractometer (Mo Kα radiation (λ=0.71073 Å) and processed using the DENZO-SMN package [Ref:. Carter C.W., and Sweet R.M. (Eds), Academic ], including inter-frame scaling (which was carried out using Scalepack within DENZO-SMN)
    • Data were collected using an Enraf-Nonius KappaCCD diffractometer (Mo Kα radiation (λ=0.71073 Å) and processed using the DENZO-SMN package [Ref:. Otwinowski Z., and Minor W. Processing of X-ray Diffraction Data Collected in Oscillation Mode. In: Carter C.W., and Sweet R.M. (Eds). Methods in Enzymology (1997), Academic 276 ], including inter-frame scaling (which was carried out using Scalepack within DENZO-SMN)
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    • Otwinowski, Z.1    Minor, W.2
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    • 2. In general, all non-hydrogen atoms were refined with anisotropic displacement parameters however, in both molecules, the atomic displacement ellipsoids for the methyl ester groups were prolate and the larger of these was modelled as disordered over two positions with isotropic displacement parameters. Hydrogen atoms were generally located in the difference map and the positions and isotropic displacement parameters were refined using restraints prior to inclusion into the model with riding constraints. For further details see the Supplementary information (CIF). Full crystallographic data have also been deposited with the Cambridge Crystallographic Data Centre, CCDC 746459. Copies of these data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif
    • 2. In general, all non-hydrogen atoms were refined with anisotropic displacement parameters however, in both molecules, the atomic displacement ellipsoids for the methyl ester groups were prolate and the larger of these was modelled as disordered over two positions with isotropic displacement parameters. Hydrogen atoms were generally located in the difference map and the positions and isotropic displacement parameters were refined using restraints prior to inclusion into the model with riding constraints. For further details see the Supplementary information (CIF). Full crystallographic data have also been deposited with the Cambridge Crystallographic Data Centre, CCDC 746459. Copies of these data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif
    • (2003) J. Appl. Crystallogr. , vol.36 , pp. 1487
    • Betteridge, P.W.1    Carruthers, J.R.2    Cooper, G.I.3    Prout, C.K.4    Watkin, D.J.5


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