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8
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85031065072
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iPBP, under the same conditions, we have now obtained the adduct with 93% ee and 95:5 dr instead of 83% ee and 95:5 dr (Ref. 4a). New experiments have revealed a problem with the optical purity of some crops of our chiral diamine, which was only 89% ee. With an optically pure diamine
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New experiments have revealed a problem with the optical purity of some crops of our chiral diamine, which was only 89% ee. With an optically pure diamine iPBP , under the same conditions, we have now obtained the adduct with 93% ee and 95:5 dr instead of 83% ee and 95:5 dr (Ref. 4a).
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9
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85031056332
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For other syntheses of racemic botryodiplodin see: (a) McMurry, P. M. J. ; Abe, K. J. Am. Chem. Soc. 1973, 95, 5824; (b) McMurry, P. M. J.; Abe, K. Tetrahedron Lett. 1973, 14, 4103; (c) Mukaiyama, T.; Wada, M.; Hanna, J. Chem. Lett. 1974, 94, 1181; (d) Wilson, S. R.; Myers, R. S. J. Org. Chem. 1975, 40, 3309; (e) Kurth, M. J.; Yu, C.-M. J. Org. Chem. 1985, 50, 1840. (f) Dulcere, J. P.; Mihoubi, M. N.; Rodriguez, J. J. Org. Chem. 1993, 58, 5709; (g) Daub, G. W. ; Edwards, J. P.; Okada, C. R.; Allen, J. W.; Maxey, C. T.; Wells, M. S.; Goldstein, A. S.; Dibley, M. J.; Wang, C. J.; Ostercamp, D. P.; Chung, S.; Cunningham, P. S.; Berliner, M. A. J. Org. Chem. 1997, 62, 1976; (h) Nouguier, R.; Gastaldi, S.; Stien, D.; Bertrand, M.; Renaud, P. Tetrahedron Lett. 1999, 40, 3371; (i) Villar, F.; Andrey, O.; Renaud, P. Tetrahedron Lett. 1999, 40, 3375.
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For other syntheses of racemic botryodiplodin see: (a) McMurry, P. M. J. ; Abe, K. J. Am. Chem. Soc. 1973, 95, 5824; (b) McMurry, P. M. J.; Abe, K. Tetrahedron Lett. 1973, 14, 4103; (c) Mukaiyama, T.; Wada, M.; Hanna, J. Chem. Lett. 1974, 94, 1181; (d) Wilson, S. R.; Myers, R. S. J. Org. Chem. 1975, 40, 3309; (e) Kurth, M. J.; Yu, C.-M. J. Org. Chem. 1985, 50, 1840. (f) Dulcere, J. P.; Mihoubi, M. N.; Rodriguez, J. J. Org. Chem. 1993, 58, 5709; (g) Daub, G. W. ; Edwards, J. P.; Okada, C. R.; Allen, J. W.; Maxey, C. T.; Wells, M. S.; Goldstein, A. S.; Dibley, M. J.; Wang, C. J.; Ostercamp, D. P.; Chung, S.; Cunningham, P. S.; Berliner, M. A. J. Org. Chem. 1997, 62, 1976; (h) Nouguier, R.; Gastaldi, S.; Stien, D.; Bertrand, M.; Renaud, P. Tetrahedron Lett. 1999, 40, 3371; (i) Villar, F.; Andrey, O.; Renaud, P. Tetrahedron Lett. 1999, 40, 3375.
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12
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0019925801
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Moreau S., Lablache-Combier A., Biguet J., Foulon C., Delfosse M. J. Org. Chem. 47:1982;2358.
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(1982)
J. Org. Chem.
, vol.47
, pp. 2358
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Moreau, S.1
Lablache-Combier, A.2
Biguet, J.3
Foulon, C.4
Delfosse, M.5
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21
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0000851805
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The Henry (nitroaldol) Reaction
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B.M. Trost, & I. Fleming. Oxford: Pergamon Press
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Rosini G. The Henry (nitroaldol) Reaction. Trost B.M., Fleming I. Comprehensive Organic Synthesis. 2:1991;321-340 Pergamon Press, Oxford.
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(1991)
Comprehensive Organic Synthesis
, vol.2
, pp. 321-340
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Rosini, G.1
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26
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0000125222
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4OAc: McMurry, J. E.; Melton, J.; Padgett, H. J. Org. Chem. 1974, 39, 259.
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27
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85031055062
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t (10-anti): 5.2, 5.6 min.
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t ( 10-anti ): 5.2, 5.6 min.
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28
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85031053491
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t (1β): 48.2 min
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t ( 1β ): 48. 2 min.
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29
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85031059046
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note
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t ( 12β ): 38.7, 39.3 min.
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