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Volumn 54, Issue 19, 1998, Pages 4761-4786

Studies on the chemoselectivity and diastereoselectivity of samarium(II) iodide mediated transformations of carbohydrate derived ω-halo-α,β- unsaturated easters

Author keywords

[No Author keywords available]

Indexed keywords

CARBOHYDRATE; ESTER DERIVATIVE; HALOGEN; REDUCING AGENT; SAMARIUM DIIODIDE; UNCLASSIFIED DRUG;

EID: 0032079609     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00191-4     Document Type: Article
Times cited : (26)

References (57)
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    • 2 reactions of unsaturated halides see references 1a and 1c and references therein. Also see Curran, D.P.; Gu, X.; Zhang, W.; Dowd, P. Tetrahedron 1997, 53, 9023-9042.
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    • 3SnH mediated radical cyclizations of ω-bromo-α,β-unsaturated ethyl esters, derived from D-ribonolactone, have been reported in the literature. See: Wilcox, C.S.; Thomasco, L.M. J. Org. Chem. 1985, 50, 546-547.
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    • 2, to promote conjugate addition reactions of alkyl halides onto α,β-unsaturated esters, amides, lactones, lactams and nitriles. See: Molander, G.A. and Harris, C.R. J. Org. Chem. 1997, 62, 7418 - 7429.
    • (1997) J. Org. Chem. , vol.62 , pp. 7418-7429
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    • note
    • (c) reference 2 (a).
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    • 11. There is literature precedent for an non-reductive reaction pathway open to type A substrates: intramolecular Michael addition of the ε -hydroxyl group onto the unsaturated ester gives terahydrofuran compounds. For an example see: Freeman, F. and Robarge, K.D. J. Org. Chem. 1989, 54, 346-359.
    • (1989) J. Org. Chem. , vol.54 , pp. 346-359
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    • Inanaga, J.1    Yamaguchi, M.2
  • 30
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    • 2 mediated transformations of carbohydrates to carbocycles via an intramolecular coupling of an aldehyde carbonyl with an α,β - unsaturated ester see: (a) Enholm, E. J. ; Trivellas, A. Tetrahedron Lett. 1994, 35, 1627-1628.
    • (1994) Tetrahedron Lett. , vol.35 , pp. 1627-1628
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    • 15. Commercially available from Aldrich.
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    • unpublished results
    • 19. The effects of various parameters on the diastereoselectivity of reductive carbocyclizations of a series of ω-halo-α, β-unsaturated esters is currently being investigated in our laboratory and will be reported in due course: Kouya Biboutou, R; Bennett, S. M. unpublished results.
    • Kouya Biboutou, R.1    Bennett, S.M.2
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    • John Wiley & Sons
    • 22 Hydrogen atom abstraction by the radical from THF, to give the simple reduction product, is also a possibility but this is expected to be much slower than either cyclization or reduction. See J. Fossey, D. Lefort, J. Sorba. Free Radicals in Organic Chemistry, John Wiley & Sons, 1995.
    • (1995) Free Radicals in Organic Chemistry
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    • 2/THF/DMPU to carry out reductive cyclizations on alkynyl iodides and bromides: Zhou, Z., Larouche, D.; Bennett, S.M. Tetrahedron, 1995, 51, 11623-11644.
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    • 26. For a discussion on the mechanisms of electrochemically mediated hydrodimerizations see: (a) Utley, J. Chem. Soc. Rev. 1997, 26, 157-167.
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    • note
    • 8 has previously been described in the literature: the choice and the order of addition of co-solvents and reagents appears to be critical to the chemoselectivity of these reactions.
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    • note
    • 1/2 = 0.072 and S = 1.49. The list of refined atomic coordinates the bond distances and angles, the calculated H positions and the structure factor table have been deposited with the Cambridge Crystallographic Data Centre, University Chemical laboratory, 12 Union Road, Cambridge, CB2 1EZ, U.K.


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