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For a review, see: (a) Magid, R. M. Tetrahedron 1980, 36, 1901-1930. (b) Toromanoff, E. Tetrahedron 1980, 36, 2809-2931. (c) Paquette, L. A.; Stirling, C. J. M. Tetrahedron 1992, 48, 7383-7423. For recent reviews on metal-catalyzed allylic substitution reactions, see: (d) Pfaltz, A.; Lautens, M., In Comprehensive Asymmetric Catalysis II; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag Telos: Berlin Heidelberg, 1999; Chapter 24, pp 833-884. (e) Trost, B. M.; Crawley, M. L. Chem. Rev. 2003, 103, 2921-2943.
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For a review, see: (a) Magid, R. M. Tetrahedron 1980, 36, 1901-1930. (b) Toromanoff, E. Tetrahedron 1980, 36, 2809-2931. (c) Paquette, L. A.; Stirling, C. J. M. Tetrahedron 1992, 48, 7383-7423. For recent reviews on metal-catalyzed allylic substitution reactions, see: (d) Pfaltz, A.; Lautens, M., In Comprehensive Asymmetric Catalysis II; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag Telos: Berlin Heidelberg, 1999; Chapter 24, pp 833-884. (e) Trost, B. M.; Crawley, M. L. Chem. Rev. 2003, 103, 2921-2943.
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For a review, see: (a) Magid, R. M. Tetrahedron 1980, 36, 1901-1930. (b) Toromanoff, E. Tetrahedron 1980, 36, 2809-2931. (c) Paquette, L. A.; Stirling, C. J. M. Tetrahedron 1992, 48, 7383-7423. For recent reviews on metal-catalyzed allylic substitution reactions, see: (d) Pfaltz, A.; Lautens, M., In Comprehensive Asymmetric Catalysis II; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag Telos: Berlin Heidelberg, 1999; Chapter 24, pp 833-884. (e) Trost, B. M.; Crawley, M. L. Chem. Rev. 2003, 103, 2921-2943.
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Paquette, L.A.1
Stirling, C.J.M.2
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4
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Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag Telos: Berlin Heidelberg, Chapter 24
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For a review, see: (a) Magid, R. M. Tetrahedron 1980, 36, 1901-1930. (b) Toromanoff, E. Tetrahedron 1980, 36, 2809-2931. (c) Paquette, L. A.; Stirling, C. J. M. Tetrahedron 1992, 48, 7383-7423. For recent reviews on metal-catalyzed allylic substitution reactions, see: (d) Pfaltz, A.; Lautens, M., In Comprehensive Asymmetric Catalysis II; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag Telos: Berlin Heidelberg, 1999; Chapter 24, pp 833-884. (e) Trost, B. M.; Crawley, M. L. Chem. Rev. 2003, 103, 2921-2943.
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Pfaltz, A.1
Lautens, M.2
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5
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For a review, see: (a) Magid, R. M. Tetrahedron 1980, 36, 1901-1930. (b) Toromanoff, E. Tetrahedron 1980, 36, 2809-2931. (c) Paquette, L. A.; Stirling, C. J. M. Tetrahedron 1992, 48, 7383-7423. For recent reviews on metal-catalyzed allylic substitution reactions, see: (d) Pfaltz, A.; Lautens, M., In Comprehensive Asymmetric Catalysis II; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag Telos: Berlin Heidelberg, 1999; Chapter 24, pp 833-884. (e) Trost, B. M.; Crawley, M. L. Chem. Rev. 2003, 103, 2921-2943.
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For an example of azetidinone substituted at the side chain with an amino group such as tabtoxin and its analogues, see: (a) Lee, D. L.; Rapoport, H. J. Org. Chem. 1975, 40, 3491-3496. (b) Baldwin, J. E.; Otsuka, M.; Wallace, P. M. Tetrahedron 1986, 42, 3097-3110. (c) Greenlee, W. J.; Springer, J. P.; Patchett, A. A. J. Med. Chem. 1989, 32, 165-170.
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For an example of azetidinone substituted at the side chain with an amino group such as tabtoxin and its analogues, see: (a) Lee, D. L.; Rapoport, H. J. Org. Chem. 1975, 40, 3491-3496. (b) Baldwin, J. E.; Otsuka, M.; Wallace, P. M. Tetrahedron 1986, 42, 3097-3110. (c) Greenlee, W. J.; Springer, J. P.; Patchett, A. A. J. Med. Chem. 1989, 32, 165-170.
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For an example of azetidinone substituted at the side chain with an amino group such as tabtoxin and its analogues, see: (a) Lee, D. L.; Rapoport, H. J. Org. Chem. 1975, 40, 3491-3496. (b) Baldwin, J. E.; Otsuka, M.; Wallace, P. M. Tetrahedron 1986, 42, 3097-3110. (c) Greenlee, W. J.; Springer, J. P.; Patchett, A. A. J. Med. Chem. 1989, 32, 165-170.
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Cardillo, G.1
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Tolomelli, A.5
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31
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14844341865
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note
-
Reaction of 1a carried out at rt afforded, in about 70 h, (E)-2a as the major isomer (56%), (Z)-3a (29%), and 4a (15%).
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-
-
-
32
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14844340236
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note
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1H NMR signal of H1′ resonating at 5.0 ppm; see Supporting Information.
-
-
-
-
34
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0022636853
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(b) Otto, H. H.; Bergmann, H. J.; Mayrhofer, R. Arch. Pharm. (Weinheim, Ger.) 1986, 319, 203-216.
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Otto, H.H.1
Bergmann, H.J.2
Mayrhofer, R.3
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35
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14844366674
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-
note
-
2 = 1.037.
-
-
-
-
36
-
-
14844365877
-
-
note
-
3 (c 1.0); Chiralcel OD (Daicel column), cellulose tris(3,5-dimethyl-phenyl)carbamate phase coated on 10 μm silica gel, n-hexane/2-propanol 90:10 solvent mixture, flow 0.5 mL/min.
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