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Iminium ions are the proposed intermediates in the reductive amination of carbonyl compounds (Review: Baxter, E. W.; Reitz, A. B. In Organic Reactions; Overman, L. E., Ed.; Wiley: New York, 2002; Vol. 59, p 1) for which reducing reagents such as sodium cyanoborohydride (Borch, R. F.; Bernstein, M. D.; Durst, H. D. J. Am. Chem. Soc. 1971, 93, 2897), sodium triacetoxyborohydride (Abdel-Magid, A. F.; Carson, K. G.; Harris, B. D.; Maryanoff, C. A.; Shah, R. D. J. Org. Chem. 1996, 61, 3849), or sodium borohydride have been recommended (e.g., Schellenberg, K. A. J. Org. Chem. 1963, 28, 3259). Trans-selective reductions of cylic imines have been reported also with sodium /ethanol (Vierhapper, F. W.; Eliel, E. L. J. Org. Chem. 1975, 40, 2734).
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Iminium ions are the proposed intermediates in the reductive amination of carbonyl compounds (Review: Baxter, E. W.; Reitz, A. B. In Organic Reactions; Overman, L. E., Ed.; Wiley: New York, 2002; Vol. 59, p 1) for which reducing reagents such as sodium cyanoborohydride (Borch, R. F.; Bernstein, M. D.; Durst, H. D. J. Am. Chem. Soc. 1971, 93, 2897), sodium triacetoxyborohydride (Abdel-Magid, A. F.; Carson, K. G.; Harris, B. D.; Maryanoff, C. A.; Shah, R. D. J. Org. Chem. 1996, 61, 3849), or sodium borohydride have been recommended (e.g., Schellenberg, K. A. J. Org. Chem. 1963, 28, 3259). Trans-selective reductions of cylic imines have been reported also with sodium /ethanol (Vierhapper, F. W.; Eliel, E. L. J. Org. Chem. 1975, 40, 2734).
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Hydrogenation over platinum on carbon, palladium on carbon and platinum oxide was also tested but resulted in an increased amount of the cis diastereomer, as precedented (e.g., refs 4 and 7).
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The term "telescoping" has been used before to describe sequential multistep/ multipot processes with shortened or omitted isolation procedures for the involved intermediates; see, e.g.: Dale, D. J.; Draper, J.; Dunn, P. J.; Hughes, M. L.; Hussain, F.; Levett, P. C.; Ward, G. B.; Wood, A. S. Org. Process Res. Dev. 2002, 6, 767.
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Other resolving reagents, such as e.g., L-tartaric acid, dibenzoyl-L-tartaric acid, L-malic acid, (S)-mandelic acid, (1S)-10- camphorsulfonic acid, had been tested for 8. The results with regard to optical purity, yield, and crystallization behavior were rated as less favorable as compared to the diastereomeric salt formation with o,o-ditoluoyl-L-tartaric acid.
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See, for example: (a) Kita, T.; Georgieva, A.; Hashimoto, Y.; Nakata, T. ; Nagasawa, K. Angew. Chem., Int. Ed. 2002, 41, 2832. (b) McDavid, P.; Chen, Y. ; Deng, L. Angew. Chem., Int. Ed. 2002, 41, 338. (c) C. Schneider, Angew. Chem., Int. Ed. 2002, 41, 744. (d) Trost, B. M.; Yeh, V. S. C. Angew. Chem., Int. Ed. 2002, 41, 861.
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See, for example: (a) Kita, T.; Georgieva, A.; Hashimoto, Y.; Nakata, T. ; Nagasawa, K. Angew. Chem., Int. Ed. 2002, 41, 2832. (b) McDavid, P.; Chen, Y. ; Deng, L. Angew. Chem., Int. Ed. 2002, 41, 338. (c) C. Schneider, Angew. Chem., Int. Ed. 2002, 41, 744. (d) Trost, B. M.; Yeh, V. S. C. Angew. Chem., Int. Ed. 2002, 41, 861.
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See, for example: (a) Kita, T.; Georgieva, A.; Hashimoto, Y.; Nakata, T. ; Nagasawa, K. Angew. Chem., Int. Ed. 2002, 41, 2832. (b) McDavid, P.; Chen, Y. ; Deng, L. Angew. Chem., Int. Ed. 2002, 41, 338. (c) C. Schneider, Angew. Chem., Int. Ed. 2002, 41, 744. (d) Trost, B. M.; Yeh, V. S. C. Angew. Chem., Int. Ed. 2002, 41, 861.
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