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For the preparation of azepines by ring-closing metathesis, cf. (a) Hoffmann, T.; Waibel, R.; Gmeiner, P. J. Org. Chem. 2003, 68, 62. (b) Wipf, P.; Rector, S. R.; Takahashi, H. J. Am. Chem. Soc. 2002, 124, 14848. (c) Furstner, A.; Guth, O.; Duffels, A.; Seidel, G.; Liebl, M.; Gabor, B.; Mynott, R. Chem. Eur. J. 2001, 7, 4811. (d) Fu, G. C.; Grubbs, R. H. J. Am. Chem. Soc. 1992, 114, 7324.
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0037132647
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For the preparation of azepines by ring-closing metathesis, cf. (a) Hoffmann, T.; Waibel, R.; Gmeiner, P. J. Org. Chem. 2003, 68, 62. (b) Wipf, P.; Rector, S. R.; Takahashi, H. J. Am. Chem. Soc. 2002, 124, 14848. (c) Furstner, A.; Guth, O.; Duffels, A.; Seidel, G.; Liebl, M.; Gabor, B.; Mynott, R. Chem. Eur. J. 2001, 7, 4811. (d) Fu, G. C.; Grubbs, R. H. J. Am. Chem. Soc. 1992, 114, 7324.
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0035914638
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For the preparation of azepines by ring-closing metathesis, cf. (a) Hoffmann, T.; Waibel, R.; Gmeiner, P. J. Org. Chem. 2003, 68, 62. (b) Wipf, P.; Rector, S. R.; Takahashi, H. J. Am. Chem. Soc. 2002, 124, 14848. (c) Furstner, A.; Guth, O.; Duffels, A.; Seidel, G.; Liebl, M.; Gabor, B.; Mynott, R. Chem. Eur. J. 2001, 7, 4811. (d) Fu, G. C.; Grubbs, R. H. J. Am. Chem. Soc. 1992, 114, 7324.
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Furstner, A.1
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0000587503
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For the preparation of azepines by ring-closing metathesis, cf. (a) Hoffmann, T.; Waibel, R.; Gmeiner, P. J. Org. Chem. 2003, 68, 62. (b) Wipf, P.; Rector, S. R.; Takahashi, H. J. Am. Chem. Soc. 2002, 124, 14848. (c) Furstner, A.; Guth, O.; Duffels, A.; Seidel, G.; Liebl, M.; Gabor, B.; Mynott, R. Chem. Eur. J. 2001, 7, 4811. (d) Fu, G. C.; Grubbs, R. H. J. Am. Chem. Soc. 1992, 114, 7324.
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0037073212
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23
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0037430515
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24
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2942678732
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Hong, S.H.1
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25
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4444272441
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note
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Exposure of A to the allylation conditions led to carbamate cleavage product B, which upon ring-closing metathesis provided the 11-membered C rather than the azepine product. Interestingly, this reaction was much faster (< 1 h) than the formation of azepines 9. (Equation Presented)
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26
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33947462653
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(a) Pappo, R.; Allen, D. S.; Lemieux, R. U.; Johnson, W. S. J. Org. Chem. 1956, 21, 478.
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27
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0028810543
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(b) Wipf, P.; Kim, Y.; Goldstein, D. M. J. Am. Chem. Soc. 1995, 117, 11106.
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2942576352
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Rudolph, A.C.1
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29
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4444311451
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note
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These observations are in agreement with the results of Rudolph et al. (ref 17); however, Lewis acidic conditions appear to promote N-dephosphinoylation and do not furnish the desired pyrrolidines in acceptable yields.
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30
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0011228398
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(a) LaLonde, R. T.; Muhammad, N.; Wong, C. F.; Sturiale, E. R. J. Org. Chem. 1980, 45, 3664.
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LaLonde, R.T.1
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Sturiale, E.R.4
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33
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0034679048
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(d) Abe, H.; Aoyagi, S.; Kibayashi, C. J. Am. Chem. Soc. 2000, 122, 4583.
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Abe, H.1
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34
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4444354869
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note
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The relative stereochemistry of 23 was assigned by NOESY and the product was assumed to arise from an inversion of configuration at the quaternary carbon atom. (Equation Presented)
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35
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4444292999
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note
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Preliminary screening of compounds 3 revealed interesting nuclear receptor binding and antiproliferative effects.
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