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HMPA and related phosphoramides are known to have the highest donicities of common solvents, see: (a) Reichardt, C. Solvents and Solvent Effects in Organic Chemistry, 2nd ed.; VCH: Weinheim, 1988; pp 17- 27. (b) Gritzner, G.; Hörzenberger, F. J. Chem. Soc., Faraday Trans. 1995, 91, 3843. (c) Gritzner, G. Z. Phys. Chem. Neue Folge 1988, 158, 99. (d) Gritzner, G. J. Mol. Liq. 1997, 487. (e) Sandström, M.; Persson, I.; Persson, P. Acta Chem. Scand. 1990, 44, 653. (f) Maria, P.-C.; Gal, J.-F.; Franceschi, J. d.; Fargin, E. J. Am. Chem. Soc. 1987, 109, 483. (g) Bassindale, A. R.; Lau, J. C.-Y.; Taylor, P. G. J. Organomet. Chem. 1995, 490, 75. (h) Bassindale, A. R.; Lau, J. C-Y.; Taylor, P. G. J. Organomet. Chem. 1995, 499, 137.
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The presence of 4 A molecular sieves in the reaction mixture has no apparent effect on the selectivity of the process, although they may prevent elimination of the trichlorosilyl aldolate.
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All X-ray crystal structure data has been deposited in the Cambridge Crystallographic Data Center as supplementary publication Nos. CCDC-111716 ((+)-anti-10), CCDC-111826 ((+)-syn-19), CCDC-111715 ((+)-syn-4b). Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB21EZ, UK (fax: (+44)1223-336-033; e-mail: deposit@ccdc.cam.ac.uk)
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All X-ray crystal structure data has been deposited in the Cambridge Crystallographic Data Center as supplementary publication Nos. CCDC-111716 ((+)-anti-10), CCDC-111826 ((+)-syn-19)), CCDC-111715 ((+)-syn-4b)). Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB21EZ, UK (fax: (+44)1223-336-033; e-mail: deposit@ccdc.cam.ac.uk).
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0344833392
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-
note
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This notation is used to describe the faces of the enol double bond relative to the C(1) (oxygen-bearing) position, rather than the more typical C(2) position which is actually transformed into the resultant tetrahedral center.
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