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Recently, Nelson reported such a process during a study of the Sharpless kinetic resolution of difuryl diols: (a) Harding, M.; Hodgson, R.: Nelson, A. J. Chem. Soc., Perkin Trans. 1 2002, 2403-2413. (b) Bartlett, S.; Hodgson, R.; Holland, J. M.; Jones, M.; Kilner, C.; Nelson, A.; Warriner, S. Org. Biomol. Chem. 2003, 1, 2393-2402.
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Recently, Nelson reported such a process during a study of the Sharpless kinetic resolution of difuryl diols: (a) Harding, M.; Hodgson, R.: Nelson, A. J. Chem. Soc., Perkin Trans. 1 2002, 2403-2413. (b) Bartlett, S.; Hodgson, R.; Holland, J. M.; Jones, M.; Kilner, C.; Nelson, A.; Warriner, S. Org. Biomol. Chem. 2003, 1, 2393-2402.
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7044271736
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note
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This was confirmed by X-ray crystallography, details of which will be provided in a full description of this work.
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7044254087
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note
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Enantiomeric excess was determined by Mosher's ester derivatization.
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21
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7044279665
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note
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1H NMR spectrum of the crude material.
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22
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0031053524
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0030876792
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For a discussion of the origins of stereocontrol in related cyclizations, see: (a) Betancort, J. M.; Martín, V. S.; Padrón, J. M.; Palazón, J. M.; Ramírez, M. A.; Soler, M. A. J. Org. Chem. 1997, 62, 4570-4583. (b) Ramírez, M. A.; Padrón J. M.; Palazón, J. M.; Martin, V. S. J. Org. Chem. 1997, 62, 4584-4590.
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Soler, M.A.6
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26
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0030852861
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For a discussion of the origins of stereocontrol in related cyclizations, see: (a) Betancort, J. M.; Martín, V. S.; Padrón, J. M.; Palazón, J. M.; Ramírez, M. A.; Soler, M. A. J. Org. Chem. 1997, 62, 4570-4583. (b) Ramírez, M. A.; Padrón J. M.; Palazón, J. M.; Martin, V. S. J. Org. Chem. 1997, 62, 4584-4590.
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0000810548
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2O; (c) LiBr, THF; see: Jung, M. E.; Miller, S. J. Heterocycles 1990, 30, 839-853.
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28
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0000810548
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note
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2O; (c) LiBr, THF; see: Jung, M. E.; Miller, S. J. Heterocycles 1990, 30, 839-853.
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For a related example of cyclization of a 3°-alkoxide, see: Nicolaou, K. C.; Hwang, C.-K.; Duggan, M. E. J. Am. Chem. Soc. 1989, 111, 6682-6690.
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