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For further examples of tandem ring rearrangement (RCM-ROM-RCM) metathesis reactions, see: a) Zuercher, W. J.; Hashimoto, M.; Grubbs, R. H. J. Am. Chem. Soc. 1996, 118, 6634-6640. b) Burke, S. D.; Quinn, K J.; Chen, V. J. J. Org. Chem. 1998, 63, 8626-8627. c) Zuercher, W. J.; Scholl, M.; Grubbs, R. H. J. Org. Chem. 1998, 63, 4291-4298. d) Weatherhead, G. S.; Ford, J. G.; Alexanian, E. J.; Schrock, R. R.; Hoveyda, A. H. J. Am. Chem. Soc. 2000, 122, 1828-1829. e) Choi, T.-L.; Grubbs, R. H. Chem. Commun. 2001, 2648-2649. f) Stapper, C.; Blechert, S. Eur. J. Org. Chem. 2002, 16, 2855-2858.
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Zuercher, W.J.1
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Grubbs, R.H.3
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14
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0031735502
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For further examples of tandem ring rearrangement (RCM-ROM-RCM) metathesis reactions, see: a) Zuercher, W. J.; Hashimoto, M.; Grubbs, R. H. J. Am. Chem. Soc. 1996, 118, 6634-6640. b) Burke, S. D.; Quinn, K J.; Chen, V. J. J. Org. Chem. 1998, 63, 8626-8627. c) Zuercher, W. J.; Scholl, M.; Grubbs, R. H. J. Org. Chem. 1998, 63, 4291-4298. d) Weatherhead, G. S.; Ford, J. G.; Alexanian, E. J.; Schrock, R. R.; Hoveyda, A. H. J. Am. Chem. Soc. 2000, 122, 1828-1829. e) Choi, T.-L.; Grubbs, R. H. Chem. Commun. 2001, 2648-2649. f) Stapper, C.; Blechert, S. Eur. J. Org. Chem. 2002, 16, 2855-2858.
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Burke, S.D.1
Quinn, K.J.2
Chen, V.J.3
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15
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0001117364
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For further examples of tandem ring rearrangement (RCM-ROM-RCM) metathesis reactions, see: a) Zuercher, W. J.; Hashimoto, M.; Grubbs, R. H. J. Am. Chem. Soc. 1996, 118, 6634-6640. b) Burke, S. D.; Quinn, K J.; Chen, V. J. J. Org. Chem. 1998, 63, 8626-8627. c) Zuercher, W. J.; Scholl, M.; Grubbs, R. H. J. Org. Chem. 1998, 63, 4291-4298. d) Weatherhead, G. S.; Ford, J. G.; Alexanian, E. J.; Schrock, R. R.; Hoveyda, A. H. J. Am. Chem. Soc. 2000, 122, 1828-1829. e) Choi, T.-L.; Grubbs, R. H. Chem. Commun. 2001, 2648-2649. f) Stapper, C.; Blechert, S. Eur. J. Org. Chem. 2002, 16, 2855-2858.
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Zuercher, W.J.1
Scholl, M.2
Grubbs, R.H.3
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16
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0034053137
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For further examples of tandem ring rearrangement (RCM-ROM-RCM) metathesis reactions, see: a) Zuercher, W. J.; Hashimoto, M.; Grubbs, R. H. J. Am. Chem. Soc. 1996, 118, 6634-6640. b) Burke, S. D.; Quinn, K J.; Chen, V. J. J. Org. Chem. 1998, 63, 8626-8627. c) Zuercher, W. J.; Scholl, M.; Grubbs, R. H. J. Org. Chem. 1998, 63, 4291-4298. d) Weatherhead, G. S.; Ford, J. G.; Alexanian, E. J.; Schrock, R. R.; Hoveyda, A. H. J. Am. Chem. Soc. 2000, 122, 1828-1829. e) Choi, T.-L.; Grubbs, R. H. Chem. Commun. 2001, 2648-2649. f) Stapper, C.; Blechert, S. Eur. J. Org. Chem. 2002, 16, 2855-2858.
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Weatherhead, G.S.1
Ford, J.G.2
Alexanian, E.J.3
Schrock, R.R.4
Hoveyda, A.H.5
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17
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0035930791
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For further examples of tandem ring rearrangement (RCM-ROM-RCM) metathesis reactions, see: a) Zuercher, W. J.; Hashimoto, M.; Grubbs, R. H. J. Am. Chem. Soc. 1996, 118, 6634-6640. b) Burke, S. D.; Quinn, K J.; Chen, V. J. J. Org. Chem. 1998, 63, 8626-8627. c) Zuercher, W. J.; Scholl, M.; Grubbs, R. H. J. Org. Chem. 1998, 63, 4291-4298. d) Weatherhead, G. S.; Ford, J. G.; Alexanian, E. J.; Schrock, R. R.; Hoveyda, A. H. J. Am. Chem. Soc. 2000, 122, 1828-1829. e) Choi, T.-L.; Grubbs, R. H. Chem. Commun. 2001, 2648-2649. f) Stapper, C.; Blechert, S. Eur. J. Org. Chem. 2002, 16, 2855-2858.
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Choi, T.-L.1
Grubbs, R.H.2
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18
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0000342722
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For further examples of tandem ring rearrangement (RCM-ROM-RCM) metathesis reactions, see: a) Zuercher, W. J.; Hashimoto, M.; Grubbs, R. H. J. Am. Chem. Soc. 1996, 118, 6634-6640. b) Burke, S. D.; Quinn, K J.; Chen, V. J. J. Org. Chem. 1998, 63, 8626-8627. c) Zuercher, W. J.; Scholl, M.; Grubbs, R. H. J. Org. Chem. 1998, 63, 4291-4298. d) Weatherhead, G. S.; Ford, J. G.; Alexanian, E. J.; Schrock, R. R.; Hoveyda, A. H. J. Am. Chem. Soc. 2000, 122, 1828-1829. e) Choi, T.-L.; Grubbs, R. H. Chem. Commun. 2001, 2648-2649. f) Stapper, C.; Blechert, S. Eur. J. Org. Chem. 2002, 16, 2855-2858.
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Stapper, C.1
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25
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0037048460
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e) Ovaa, H.; Stapper, C.; van der Marel, G. A.; Overkleeft, H. S.; van Boom, J. H.; Blechert, S. Tetrahedron 2002, 37, 7503-7518.
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For further examples of [2,3]-Wittig-Still rearrangements, see: a) Ovaa, H.; Lastdrager, H. B.; Codee, J. D. C.; van der Marel, G. A.; Overkleeft, H. S.; van Boom, J. H. J. Chem. Soc., Perkin Trans. 1 2002, 21, 2370-2377. b) Riether, D.; Mulzer, J. Org. Lett. 2000, 2, 3139-3141.
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Van der Marel, G.A.4
Overkleeft, H.S.5
Van Boom, J.H.6
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32
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0001066825
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For further examples of [2,3]-Wittig-Still rearrangements, see: a) Ovaa, H.; Lastdrager, H. B.; Codee, J. D. C.; van der Marel, G. A.; Overkleeft, H. S.; van Boom, J. H. J. Chem. Soc., Perkin Trans. 1 2002, 21, 2370-2377. b) Riether, D.; Mulzer, J. Org. Lett. 2000, 2, 3139-3141.
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0242391573
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Takeakin, N.; Ichiya, N.; Yoshiki, O.; Okiko, M. Tetrahedron 2000, 34, 6199-6208.
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Takeakin, N.1
Ichiya, N.2
Yoshiki, O.3
Okiko, M.4
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36
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0242391574
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-
note
-
As an analogue of 3, we synthesized Boc-piperidine and mixed it with 1 equiv of 3-phenylpropinoyl-piperidine. The mixture was dissolved in methylene chloride and treated with TFA. After 1 h the Boc-group was cleaved, while the triple bond had not reacted, as indicated by TLC and a NMR analysis of the crude mixture. After subsequent hydrogenation with Lindlar catalyst in methanol for 12 h at room temperature and conventional workup, the NMR spectra of the reaction residue showed the unchanged TFA salt of piperidine, together with stereoselective formation of the cis-cinammoyl protected piperidine in high yield.
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41
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Scholl, M.; Ding, S.; Lee, C. W.; Grubbs, R. H. Org. Lett. 1999, 1, 953-956.
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Scholl, M.1
Ding, S.2
Lee, C.W.3
Grubbs, R.H.4
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