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Trost, B. M., Fleming, I., Eds.; Pergamon Press: Elmsford, NY
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For a review on ammonium ylide, see: Markó, I. E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Elmsford, NY, 1991; p 913. For a recent review on asymmetric ylide chemistry, see: Aggarwal, V. K.; Li, A. H.; Dai, L. X. Chem. Rev. 1997, 97, 2341.
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For a review on ammonium ylide, see: Markó, I. E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Elmsford, NY, 1991; p 913. For a recent review on asymmetric ylide chemistry, see: Aggarwal, V. K.; Li, A. H.; Dai, L. X. Chem. Rev. 1997, 97, 2341.
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(b) Aggarwal, V. K.; Coogan, M. P.; Stenson, R. A.; Jones, R. V. H; Fieldhouse, R.; Blacker, J. Eur. J. Org. Chem. 2002, 2, 319.
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2Ph are 30.8 and 18.8, respectively: Cheng, J. P.; Liu, B; Zhao, Y. Y.; Sun, Y.; Zhang, X; Lu, Y. J. Org. Chem. 1999, 64, 604.
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0141550141
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note
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We have tried MeONa and pseudo-ephedrine salts made from 1 equiv of (1R,2R)-pseudo-ephedrine/1 equiv of LiHMDS or NaHMDS and 1 equiv of (1R,2R)-pseudo-ephendrine/2 equiv of n-BuLi as additives in THF solution at 0°C. In all cases, no neutral amines were obtained after workup.
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19
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33748663369
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(a) Khruscheva, N. S.; Loim, N. M.; Sokolov, V. L.; Makhaev, V. D. J. Chem. Soc., Perkin Trans. 1 1997, 2425.
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Khruscheva, N.S.1
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Sokolov, V.L.3
Makhaev, V.D.4
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0000925101
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(b) Huche, M.; Aubouet, J.; Pourcelot, G.; Berlan, J. Tetrahedron Lett. 1983, 24, 585.
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Tetrahedron Lett.
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Huche, M.1
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21
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0001640064
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(c) Hassan, A.; Rene, G.; Robert, C. Tetrahedron Lett. 1982, 23, 503.
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Tetrahedron Lett.
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Hassan, A.1
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(d) Mangeney, P.; Alexakis, A.; Normant, J. F. Tetrahedron, 1984, 40, 1803.
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Tetrahedron
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Mangeney, P.1
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25
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0028911643
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For other examples of rearrangements of ammonium ylides to give eight-membered rings, see: (a) Clark, J. S.; Hodgson, P. B. Tetrahedron Lett. 1995, 36, 2519. (b) Wright, D. L.; Weekly, R. M.; Groff, R.; McMills, M. C. Tetrahedron Lett. 1996, 37, 2165. (c) Vedejs, E.; Hagen, J. P.; Roach, B. L.; Spear, K. L. J. Org. Chem. 1978, 43, 1185.
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Clark, J.S.1
Hodgson, P.B.2
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26
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0029930972
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For other examples of rearrangements of ammonium ylides to give eight-membered rings, see: (a) Clark, J. S.; Hodgson, P. B. Tetrahedron Lett. 1995, 36, 2519. (b) Wright, D. L.; Weekly, R. M.; Groff, R.; McMills, M. C. Tetrahedron Lett. 1996, 37, 2165. (c) Vedejs, E.; Hagen, J. P.; Roach, B. L.; Spear, K. L. J. Org. Chem. 1978, 43, 1185.
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Wright, D.L.1
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McMills, M.C.4
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27
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0001131525
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For other examples of rearrangements of ammonium ylides to give eight-membered rings, see: (a) Clark, J. S.; Hodgson, P. B. Tetrahedron Lett. 1995, 36, 2519. (b) Wright, D. L.; Weekly, R. M.; Groff, R.; McMills, M. C. Tetrahedron Lett. 1996, 37, 2165. (c) Vedejs, E.; Hagen, J. P.; Roach, B. L.; Spear, K. L. J. Org. Chem. 1978, 43, 1185.
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Vedejs, E.1
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Spear, K.L.4
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28
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0141438612
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note
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For another example in which one diastereoisomer of an ylide undergoes [2,3] rearrangement and the other diastereomer undergoes a [1,2] rearrangement, see ref 18b.
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29
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33846971478
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Ylide 15 would not be expected to undergo Stevens rearrangement, as [2,3] sigmatropic rearrangements are generally faster processes than [1,2] rearrangements. Mageswaran, S.; Ollis, W. D.; Sutherland, I. O.; Thebtaranonth, Y. J. Chem. Soc., Chem. Commun. 1971, 1494. For a review on Stevens rearrangements, see ref 2.
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(a) Chelucci, G.; Saba, A.; Valenti, R.; Bacchi, A. Tetrahedron: Asymmetry 2000, 11, 3449.
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Chelucci, G.1
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32
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0000017190
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For other examples of ylides derived from acetals/thioacetals undergoing effectively a [1,2] rearrangement, see: (a) Doyle, M. P.; Griffin, J. H.; Chinn, M. S.; Leusen, D. V. J. Org. Chem. 1984, 49, 1917. (b) Trauner, D.; Porth, S.; Opatz, T.; Bats, J. W.; Giester, G.; Mülzer, J. Synthesis 1998, 653. (c) Mülzer, J.; Trauner, D.; Bats, J. W. Angew. Chem., Int. Ed. Engl. 1996, 35, 1970.
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Leusen, D.V.4
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33
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0031597451
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For other examples of ylides derived from acetals/thioacetals undergoing effectively a [1,2] rearrangement, see: (a) Doyle, M. P.; Griffin, J. H.; Chinn, M. S.; Leusen, D. V. J. Org. Chem. 1984, 49, 1917. (b) Trauner, D.; Porth, S.; Opatz, T.; Bats, J. W.; Giester, G.; Mülzer, J. Synthesis 1998, 653. (c) Mülzer, J.; Trauner, D.; Bats, J. W. Angew. Chem., Int. Ed. Engl. 1996, 35, 1970.
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Trauner, D.1
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Bats, J.W.4
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Mülzer, J.6
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34
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0029904822
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For other examples of ylides derived from acetals/thioacetals undergoing effectively a [1,2] rearrangement, see: (a) Doyle, M. P.; Griffin, J. H.; Chinn, M. S.; Leusen, D. V. J. Org. Chem. 1984, 49, 1917. (b) Trauner, D.; Porth, S.; Opatz, T.; Bats, J. W.; Giester, G.; Mülzer, J. Synthesis 1998, 653. (c) Mülzer, J.; Trauner, D.; Bats, J. W. Angew. Chem., Int. Ed. Engl. 1996, 35, 1970.
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