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For examples of well-known cyclopropyl derivatives, see: Lin, H. W.; Walsh, C. T. In The Chemistry of the Cyclopropyl Group; Patai, S., Rappoport, Z., Eds.; Wiley: New York, 1987; Vol. 16. Martel, J. In Chirality in Industry; Collins, A. N., Sheldrake, N. G., Crosby, J., Eds.; Wiley: Chichester, U.K., 1992; Chapter 4 and references therein. Barrett, A. G. M.; Kasdorf, J. J. Am. Chem. Soc. 1996, 118, 11030-11037 and references therein. Charette, A. B.; Lebel, H. J. Am. Chem. Soc. 1996, 118, 10327-10328 and references therein.
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For examples of Michael addition of nucleophiles to α,β-unsaturated ketones and esters followed by intramolecular cyclization, see: Salaun, J. Chem. Rev. 1989, 89, 1247-1270. Li, A.-H.; Dai, L.-X.; Aggarwal, V. K. Chem. Rev. 1997, 97, 2341-2372 and references therein. Krief, A.; Provins, L.; Froidbise, A. Tetrahedron Lett. 1998, 39, 1437-1440. For synthesis via cationic intermediates, see: Taylor, R. E.; Engelhardt, F. C.; Schmitt, M. J.; Yuan, H. J. Am. Chem. Soc. 2001, 123, 2964-2969. Avery, T. D.; Taylor, D. K.; Tiekink, E. R. T. J. Org. Chem. 2000, 65, 5531-5546. Avery, T. D.; Fallon, G.; Greatrex, B. W.; Pyke, S. M.; Taylor, D. K.; Tiekink, E. R. T. J. Org. Chem. 2001, 66, 7955-7966. Kimber, M. C.; Taylor, D. K. J. Org. Chem. 2002, 67, 3142-3144 and references therein.
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13C-deshielding (Δδ = 12.73 ppm). This result could be accounted for in terms of a low carbenoid character (Boche, G.; Lohrenz, J. C. W. Chem. Rev. 2001, 101, 697-756) associated with the above-mentioned Li/Cl carbenoid species (in contrast to a higher one found in the case of the 2-chloromethyl-2-oxazoline; see ref 1) that would justify its greater thermodynamic stability and a less pronounced tendency toward an "eliminative dimerization" process so typical of carbenoid species.
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note
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NOESY phase-sensitive experiments performed on compounds 8, 12a, and 13a also showed that, as a general pattern, the most deshielded cyclopropane ring hydrogen was always the one between the two heterocyclic rings, and that an oxazoline ring had, on the other hydrogen, a greater shielding effect with respect to a phenyl-substituted ring.
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(b) Abbotto, A.; Bradamante, S.; Pagani, G. A. J. Org. Chem. 1993, 58, 449-455.
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85056022271
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note
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3)} was prepared as reported in the case of 20a (see ref 4d).
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