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0003416748
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Pergamon Press, Oxford
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For general reviews see: [1a] R. M. Williams, Synthesis of Optically Active Amino Acids, Pergamon Press, Oxford, 1989. [1b] R. O. Duthaler, Tetrahedron 1994, 50, 1539-1650. [1c] M. Goodman, S. Ro, in: Burger's Medicinal Chemistry and Drug Discovery, 5th ed. (Ed.: M. Wolff), Wiley and Sons, New York, 1995, pp. 803-861. [1d] S. Hanessian, G. McNaughton-Smith, H.-G. Lombart, W. D. Lubell, Tetrahedron 1997, 53, 12789- 12854.
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For general reviews see: [1a] R. M. Williams, Synthesis of Optically Active Amino Acids, Pergamon Press, Oxford, 1989. [1b] R. O. Duthaler, Tetrahedron 1994, 50, 1539-1650. [1c] M. Goodman, S. Ro, in: Burger's Medicinal Chemistry and Drug Discovery, 5th ed. (Ed.: M. Wolff), Wiley and Sons, New York, 1995, pp. 803-861. [1d] S. Hanessian, G. McNaughton-Smith, H.-G. Lombart, W. D. Lubell, Tetrahedron 1997, 53, 12789- 12854.
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For general reviews see: [1a] R. M. Williams, Synthesis of Optically Active Amino Acids, Pergamon Press, Oxford, 1989. [1b] R. O. Duthaler, Tetrahedron 1994, 50, 1539-1650. [1c] M. Goodman, S. Ro, in: Burger's Medicinal Chemistry and Drug Discovery, 5th ed. (Ed.: M. Wolff), Wiley and Sons, New York, 1995, pp. 803-861. [1d] S. Hanessian, G. McNaughton-Smith, H.-G. Lombart, W. D. Lubell, Tetrahedron 1997, 53, 12789- 12854.
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For general reviews see: [1a] R. M. Williams, Synthesis of Optically Active Amino Acids, Pergamon Press, Oxford, 1989. [1b] R. O. Duthaler, Tetrahedron 1994, 50, 1539-1650. [1c] M. Goodman, S. Ro, in: Burger's Medicinal Chemistry and Drug Discovery, 5th ed. (Ed.: M. Wolff), Wiley and Sons, New York, 1995, pp. 803-861. [1d] S. Hanessian, G. McNaughton-Smith, H.-G. Lombart, W. D. Lubell, Tetrahedron 1997, 53, 12789-12854.
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See for example: [2a] J. S. Panek, C. E. Masse, Angew. Chem. Int. Ed. 1999, 38, 1093-1095. [2b] E. J. Corey, W. Li, G. A. Reichard, J. Am. Chem. Soc. 1998, 120, 2330-2336. [2c] E. J. Corey, W. Li, T. Nagamitsu, Angew. Chem. Int. Ed. 1998, 110, 1784-1787. [2d] H. Uno, J. E. Baldwin, A. T. Russell, J. Am. Chem. Soc. 1994, 116, 2139-2140. [2e] T. Nagamitsu, T. Sunazuka, S. Omura, P. A. Sprengler, A. B. Smith III, J. Am. Chem. Soc. 1996, 118, 3584-3590. [2f] N. Chida, J. Takeoka, N. Tsutsumi, S. Ogawa, Chem. Commun. 1995, 793-794.
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Corey, E.J.1
Li, W.2
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8
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0001406020
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See for example: [2a] J. S. Panek, C. E. Masse, Angew. Chem. Int. Ed. 1999, 38, 1093-1095. [2b] E. J. Corey, W. Li, G. A. Reichard, J. Am. Chem. Soc. 1998, 120, 2330-2336. [2c] E. J. Corey, W. Li, T. Nagamitsu, Angew. Chem. Int. Ed. 1998, 110, 1784-1787. [2d] H. Uno, J. E. Baldwin, A. T. Russell, J. Am. Chem. Soc. 1994, 116, 2139-2140. [2e] T. Nagamitsu, T. Sunazuka, S. Omura, P. A. Sprengler, A. B. Smith III, J. Am. Chem. Soc. 1996, 118, 3584-3590. [2f] N. Chida, J. Takeoka, N. Tsutsumi, S. Ogawa, Chem. Commun. 1995, 793-794.
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Sunazuka, T.2
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Sprengler, P.A.4
Smith A.B. III5
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0028914644
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See for example: [2a] J. S. Panek, C. E. Masse, Angew. Chem. Int. Ed. 1999, 38, 1093-1095. [2b] E. J. Corey, W. Li, G. A. Reichard, J. Am. Chem. Soc. 1998, 120, 2330-2336. [2c] E. J. Corey, W. Li, T. Nagamitsu, Angew. Chem. Int. Ed. 1998, 110, 1784-1787. [2d] H. Uno, J. E. Baldwin, A. T. Russell, J. Am. Chem. Soc. 1994, 116, 2139-2140. [2e] T. Nagamitsu, T. Sunazuka, S. Omura, P. A. Sprengler, A. B. Smith III, J. Am. Chem. Soc. 1996, 118, 3584-3590. [2f] N. Chida, J. Takeoka, N. Tsutsumi, S. Ogawa, Chem. Commun. 1995, 793-794.
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A synthesis of benzyl (2S,3R)-N-(benzyloxycarbonyl)-2,3-dimetnylaziridine-2-carboxylate is reported in ref.[5e]
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A synthesis of benzyl (2S,3R)-N-(benzyloxycarbonyl)-2,3-dimetnylaziridine-2-carboxylate is reported in ref.[5e]
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2O, only the starting aziridine was recovered
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2O, only the starting aziridine was recovered.
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43
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0343484637
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As both C2 and C3 positions are not activated for the substitution, the solvent plays a crucial role. In DMF the reaction proceeds with lower yield and requires more Lewis acid than in dichloromethane. In these conditions the C2 attack is favoured, probably owing to the coordinating effect of DMF. Acetonitrile shows an intermediate behaviour, affording a regioisomeric mixture. With 3-phenyl-substituted aziridines (see further) different results are obtained because the phenyl group stabilises the incipient carbocation at C3 and the solvent effect is over-whelmed, so that the C2 attack is never observed
-
As both C2 and C3 positions are not activated for the substitution, the solvent plays a crucial role. In DMF the reaction proceeds with lower yield and requires more Lewis acid than in dichloromethane. In these conditions the C2 attack is favoured, probably owing to the coordinating effect of DMF. Acetonitrile shows an intermediate behaviour, affording a regioisomeric mixture. With 3-phenyl-substituted aziridines (see further) different results are obtained because the phenyl group stabilises the incipient carbocation at C3 and the solvent effect is over-whelmed, so that the C2 attack is never observed.
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