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Aza-Cope-Mannich reactions have also been initiated by elimination of a leaving group to form the iminium cation. See, for example: (a) Overman, L. E, Jacobsen, E. J. Tetrahedron Lett. 1982, 23, 2741
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Aza-Cope-Mannich reactions have also been initiated by elimination of a leaving group to form the iminium cation. See, for example: (a) Overman, L. E.; Jacobsen, E. J. Tetrahedron Lett. 1982, 23, 2741.
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For recent applications of the aza-Cope rearrangement-Mannich cyclization in the synthesis of natural products, see: (a) Earley, W. G, Jacobsen, J. E, Madlin, A, Meier, G. P, O'Donnell, C. J, Oh, T, Old, D. W, Overman, L. E, Sharp, M. J. J. Am. Chem. Soc. 2005, 127, 18046
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For recent applications of the aza-Cope rearrangement-Mannich cyclization in the synthesis of natural products, see: (a) Earley, W. G.; Jacobsen, J. E.; Madlin, A.; Meier, G. P.; O'Donnell, C. J.; Oh, T.; Old, D. W.; Overman, L. E.; Sharp, M. J. J. Am. Chem. Soc. 2005, 127, 18046.
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For examples of imine or iminium cation formation using microwave-assisted methods, see: (a) Shi, L.; Tu, Y.-Q.; Wang, M.; Zhang, F.-M.; Fan, C.-A. Org. Lett. 2004, 6, 1001.
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34247128924
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Relative stereochemistry was confirmed by NOE analysis of 10b. MeMgBr addition to 9a and 9b followed by benzyl or benzhydryl deprotection yielded the same pyrrolidine.
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Relative stereochemistry was confirmed by NOE analysis of 10b. MeMgBr addition to 9a and 9b followed by benzyl or benzhydryl deprotection yielded the same pyrrolidine.
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42
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34247115375
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For an excellent discussion of the possible pathways for erosion of stereoselectivity in the aza-Cope-Mannich reaction, see ref. 4d
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For an excellent discussion of the possible pathways for erosion of stereoselectivity in the aza-Cope-Mannich reaction, see ref. 4d
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43
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For reviews of allylic strain-directed reactions, see: a
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