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See for example: (a) Furuta, T.; Takahashi, H.; Kasuya, Y. J. Am. Chem. Soc. 1990, 112, 3633; (b) Stevenson, D. E.; Akhtar, M.; Gani, D. Tetrahedron Lett. 1986, 27, 5661; (c) Baldwin, J. E.; Adlington, R. M.; Ting, H. H.; Arigoni, D.; Graf, P.; Martinoni, B. Tetrahedron 1985, 41, 3339.
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Furuta, T.1
Takahashi, H.2
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See for example: (a) Furuta, T.; Takahashi, H.; Kasuya, Y. J. Am. Chem. Soc. 1990, 112, 3633; (b) Stevenson, D. E.; Akhtar, M.; Gani, D. Tetrahedron Lett. 1986, 27, 5661; (c) Baldwin, J. E.; Adlington, R. M.; Ting, H. H.; Arigoni, D.; Graf, P.; Martinoni, B. Tetrahedron 1985, 41, 3339.
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Tetrahedron Lett.
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Stevenson, D.E.1
Akhtar, M.2
Gani, D.3
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3
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0021970812
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See for example: (a) Furuta, T.; Takahashi, H.; Kasuya, Y. J. Am. Chem. Soc. 1990, 112, 3633; (b) Stevenson, D. E.; Akhtar, M.; Gani, D. Tetrahedron Lett. 1986, 27, 5661; (c) Baldwin, J. E.; Adlington, R. M.; Ting, H. H.; Arigoni, D.; Graf, P.; Martinoni, B. Tetrahedron 1985, 41, 3339.
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(1985)
Tetrahedron
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Baldwin, J.E.1
Adlington, R.M.2
Ting, H.H.3
Arigoni, D.4
Graf, P.5
Martinoni, B.6
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5
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0032858326
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-
This can be particularly effective if multiply-labelled systems can be accessed, see for example: (a) Raap, J.; Nieuwenhuis, S.; Creemers, A.; Hexspoor, S.; Kragl, U.; Lugtenburg, J. Eur. J. Org. Chem. 1999, 10, 2609; (b) Gardner, K. H.; Kay, L. E. J. Am. Chem. Soc. 1997, 119, 7599; (c) Lastra, E.; Hegedus, L. S. J. Am. Chem. Soc. 1993, 115, 87.
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Eur. J. Org. Chem.
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Raap, J.1
Nieuwenhuis, S.2
Creemers, A.3
Hexspoor, S.4
Kragl, U.5
Lugtenburg, J.6
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6
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-
0030824756
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-
This can be particularly effective if multiply-labelled systems can be accessed, see for example: (a) Raap, J.; Nieuwenhuis, S.; Creemers, A.; Hexspoor, S.; Kragl, U.; Lugtenburg, J. Eur. J. Org. Chem. 1999, 10, 2609; (b) Gardner, K. H.; Kay, L. E. J. Am. Chem. Soc. 1997, 119, 7599; (c) Lastra, E.; Hegedus, L. S. J. Am. Chem. Soc. 1993, 115, 87.
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J. Am. Chem. Soc.
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Gardner, K.H.1
Kay, L.E.2
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7
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0002523403
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This can be particularly effective if multiply-labelled systems can be accessed, see for example: (a) Raap, J.; Nieuwenhuis, S.; Creemers, A.; Hexspoor, S.; Kragl, U.; Lugtenburg, J. Eur. J. Org. Chem. 1999, 10, 2609; (b) Gardner, K. H.; Kay, L. E. J. Am. Chem. Soc. 1997, 119, 7599; (c) Lastra, E.; Hegedus, L. S. J. Am. Chem. Soc. 1993, 115, 87.
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J. Am. Chem. Soc.
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, pp. 87
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Lastra, E.1
Hegedus, L.S.2
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8
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0030846447
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-
For recent reviews on the synthesis of labelled amino acids see, (a) Kelly, N. M.; Sutherland, A.; Willis, C. L. Nat. Prod. Rep. 1997, 14, 205; (b) Pshenichnikova, A. B.; Karnaukhova, E. N.; Zvonkova, E. N.; Shvets, V. I. Bioorg. Khim. 1995, 21, 163.
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Kelly, N.M.1
Sutherland, A.2
Willis, C.L.3
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9
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0000096810
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For recent reviews on the synthesis of labelled amino acids see, (a) Kelly, N. M.; Sutherland, A.; Willis, C. L. Nat. Prod. Rep. 1997, 14, 205; (b) Pshenichnikova, A. B.; Karnaukhova, E. N.; Zvonkova, E. N.; Shvets, V. I. Bioorg. Khim. 1995, 21, 163.
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Pshenichnikova, A.B.1
Karnaukhova, E.N.2
Zvonkova, E.N.3
Shvets, V.I.4
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10
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0023219599
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See for example: (a) Reider, P. J.; Conn, R. S. E.; Davis, P.; Grenda, V. J.; Zambito, A. J.; Grabowski, E. J. J. J. Org. Chem. 1987, 52, 3326; (b) Jones, J. B. Tetrahedron 1986, 42, 3351; (c) Fujihara, H.; Schowen, R. L. J. Org. Chem. 1984, 49, 2819.
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J. Org. Chem.
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Reider, P.J.1
Conn, R.S.E.2
Davis, P.3
Grenda, V.J.4
Zambito, A.J.5
Grabowski, E.J.J.6
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11
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0000714772
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See for example: (a) Reider, P. J.; Conn, R. S. E.; Davis, P.; Grenda, V. J.; Zambito, A. J.; Grabowski, E. J. J. J. Org. Chem. 1987, 52, 3326; (b) Jones, J. B. Tetrahedron 1986, 42, 3351; (c) Fujihara, H.; Schowen, R. L. J. Org. Chem. 1984, 49, 2819.
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(1986)
Tetrahedron
, vol.42
, pp. 3351
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Jones, J.B.1
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12
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0000712086
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See for example: (a) Reider, P. J.; Conn, R. S. E.; Davis, P.; Grenda, V. J.; Zambito, A. J.; Grabowski, E. J. J. J. Org. Chem. 1987, 52, 3326; (b) Jones, J. B. Tetrahedron 1986, 42, 3351; (c) Fujihara, H.; Schowen, R. L. J. Org. Chem. 1984, 49, 2819.
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J. Org. Chem.
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Fujihara, H.1
Schowen, R.L.2
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14
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0000285219
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See for example: (a) Mosin, O. V.; Skladnev, D. A.; Shvets, V. I. Biosci. Biotech. Bioch. 1998, 62, 225; (b) Milne, J. J.; Malthouse, J. P. G. Biochem. Soc. Trans. 1996, 24, 133S; (c) Faleev, N. G.; Ruvinov, S. B.; Saporovskaya, M. B.; Belikov, V. M.; Zakomyrdina, L. N.; Sakharova, I. S.; Torchinsky, Y. M. Tetrahedron Lett. 1990, 31, 7051.
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Mosin, O.V.1
Skladnev, D.A.2
Shvets, V.I.3
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15
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0030061486
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See for example: (a) Mosin, O. V.; Skladnev, D. A.; Shvets, V. I. Biosci. Biotech. Bioch. 1998, 62, 225; (b) Milne, J. J.; Malthouse, J. P. G. Biochem. Soc. Trans. 1996, 24, 133S; (c) Faleev, N. G.; Ruvinov, S. B.; Saporovskaya, M. B.; Belikov, V. M.; Zakomyrdina, L. N.; Sakharova, I. S.; Torchinsky, Y. M. Tetrahedron Lett. 1990, 31, 7051.
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Milne, J.J.1
Malthouse, J.P.G.2
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0025188088
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See for example: (a) Mosin, O. V.; Skladnev, D. A.; Shvets, V. I. Biosci. Biotech. Bioch. 1998, 62, 225; (b) Milne, J. J.; Malthouse, J. P. G. Biochem. Soc. Trans. 1996, 24, 133S; (c) Faleev, N. G.; Ruvinov, S. B.; Saporovskaya, M. B.; Belikov, V. M.; Zakomyrdina, L. N.; Sakharova, I. S.; Torchinsky, Y. M. Tetrahedron Lett. 1990, 31, 7051.
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(1990)
Tetrahedron Lett.
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, pp. 7051
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Faleev, N.G.1
Ruvinov, S.B.2
Saporovskaya, M.B.3
Belikov, V.M.4
Zakomyrdina, L.N.5
Sakharova, I.S.6
Torchinsky, Y.M.7
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84986674631
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Seebach D., Dziadulewicz E., Behrendt L., Cantoreggi S., Fitzi R. Liebigs Ann. Chem. 1989;1215.
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Seebach, D.1
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Lygo B., Crosby J., Lowdon T.R., Peterson J.A., Wainwright P.G. Tetrahedron. 57:2001;2403.
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Wainwright, P.G.5
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0002987279
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. For an authoritative review of the literature relating to the use of chiral PTCs in the asymmetric alkylation of benzophenone glycine imines see, O'Donnell M.J. Aldrichim. Acta. 34:2001;1.
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Aldrichim. Acta
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O'Donnell, M.J.1
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0003533112
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New York: Chapman and Hall. chapter 3
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. Similar observations have been noted with phenylacetonitrile, see: Starks C.M., Liotta C.L., Halpern M.C. Phase-Transfer Catalysis - Fundamentals, Applications, and Industrial Perspectives. 1994;99-100 Chapman and Hall, New York. chapter 3.
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Phase-Transfer Catalysis - Fundamentals, Applications, and Industrial Perspectives
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Starks, C.M.1
Liotta, C.L.2
Halpern, M.C.3
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33
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0001084339
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M.E. Halpern. Washington, DC: ACS
-
. For more detailed discussions on the mechanisms that may be operating in alkylations of this type see: Esikova I.A., Nahreini T.S., O'Donnell M.J. Halpern M.E., ACS Symposium Series 659: Phase-Transfer Catalysis - Mechanisms and Syntheses. 1997;89 ACS, Washington, DC.
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ACS Symposium Series 659: Phase-Transfer Catalysis - Mechanisms and Syntheses
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Esikova, I.A.1
Nahreini, T.S.2
O'Donnell, M.J.3
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34
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0011196603
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note
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4) and concentration under reduced pressure gives the crude amino acid tert-butyl ester which can generally be purified by passing through a plug of silica.
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