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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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9
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0000973977
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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.
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8. For examples of carbon-carbon double bond reduction see: (a) Inanaga, J, Sakai, S., Handa, Y., Yamaguchi, M., Yokoyama, Y. Chem. Lett. 1991, 2117-2118.
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(c) reference 2 (a).
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2 see : (a) Molander, G.A.; La Belle, B.E.; Hahn, G. J. Org. Chem. 1986, 51, 5259-5264.
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(b) Otsubo, K.; Inanaga, J.; Yamaguchi, M. Tetrahedron Lett. 1987, 28, 4437-4440.
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2 mediated hydrodimerizations see: (a) Inanaga, J., Handa, Y., Tabuchi, T, Otsubo, K., Yamaguchi, M., Hanamoto, T. Tetrahedron Lett. 1991, 32, 6557-6558.
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33845182951
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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.
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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.
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17. For an example see: Nishida, M., Ueyama, E., Hayashi, H., Ohtake, Y., Yamaura, Y., Yanaginuma, E., Yonemitsu, O., Nishida, A., Kawahara, N. J. Am. Chem. Soc. 1994, 116, 6455-6456.
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unpublished results
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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.
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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.
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46
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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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0010584943
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note
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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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56
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32. SHELXTL (PC version, 1993), Siemens, Madison, Wisconsin, USA.
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0010587196
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note
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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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