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13C NMR spectra of compounds 8, 9, 10, 11, 12, 13, 14, and 15 in which a N-Cbz group is present, showed doubling of signals. This was due to restricted rotation around the N-C=O bond, see: (a) Applications of NMR Spectroscopy in Organic Chemistry; Jackman, L. M., Sternhell, S., Eds.; Pergamon Press: Elmsford, NY, 1978; p 361.
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53
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While our work was in progress, Hanessian et al. have reported the synthesis of 3a-methoxy-N-Bus bicyclic oxapiperidine, analogous to compound 12, using different methodology, see: Loiseleur, O, Ritson, D, Nina, M, Crowley, P, Wagner, T, Hanessian, S. J. Org. Chem. 2007, 72, 6353-6363
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While our work was in progress, Hanessian et al. have reported the synthesis of 3a-methoxy-N-Bus bicyclic oxapiperidine, analogous to compound 12, using different methodology, see: Loiseleur, O.; Ritson, D.; Nina, M.; Crowley, P.; Wagner, T.; Hanessian, S. J. Org. Chem. 2007, 72, 6353-6363.
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