Asymmetric Syntheses of Both Enantiomers of α-Benzylserine and α-Carboxymethylserine

Synlett

Volumn 1997, Issue 3, 1997, Pages 253-254

  Horikawa, Manabu ^a   Nakajima, Terumi ^a   Ohfune, Yasufumi ^b  

^a SUNTORY INSTITUTE FOR BIOORGANIC RESEARCH   (Japan)

^b Osaka Prefecture University   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0037649591     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-786     Document Type: Article

References (26)

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14. For the synthesis of racemic-α-substituted serines; (a) Calcagni, A.; Rossi, D.; Lucente, G. Synthesis 1981, 445. (b) Kaminski, Z. J.; Leplawy, M. T.; Zabrocki, J. Synthesis 1973, 792. (c) Dodsworth, D. D.; Pekerar, S. V.; Requis, R.; Fiedler, P.; Garbarino, J. A.; Piovano, M. Rev. Latinoam. Quim. 1985, 16, 37. For approaches to the chiral synthesis of α-substituted serines; (a) Groth, U.; Chiang, Y-C.; Schollkopf, U. Liebigs Ann. Chem. 1982, 1756. (b) Seebach, D.; Aebi, J. D.; Gander- Coquoz, M.; Naef, R. Helv. Chim. Acta 1987, 70, 1194. (c) Ito, Y.; Sawamura, M.; Shirakawa, E.; Hayashizaki, K.; Hayashi, T. Tetrahedron Lett. 1988, 29, 235.
15. For the synthesis of racemic-α-substituted serines; (a) Calcagni, A.; Rossi, D.; Lucente, G. Synthesis 1981, 445. (b) Kaminski, Z. J.; Leplawy, M. T.; Zabrocki, J. Synthesis 1973, 792. (c) Dodsworth, D. D.; Pekerar, S. V.; Requis, R.; Fiedler, P.; Garbarino, J. A.; Piovano, M. Rev. Latinoam. Quim. 1985, 16, 37. For approaches to the chiral synthesis of α-substituted serines; (a) Groth, U.; Chiang, Y-C.; Schollkopf, U. Liebigs Ann. Chem. 1982, 1756. (b) Seebach, D.; Aebi, J. D.; Gander- Coquoz, M.; Naef, R. Helv. Chim. Acta 1987, 70, 1194. (c) Ito, Y.; Sawamura, M.; Shirakawa, E.; Hayashizaki, K.; Hayashi, T. Tetrahedron Lett. 1988, 29, 235.
16. For the synthesis of racemic-α-substituted serines; (a) Calcagni, A.; Rossi, D.; Lucente, G. Synthesis 1981, 445. (b) Kaminski, Z. J.; Leplawy, M. T.; Zabrocki, J. Synthesis 1973, 792. (c) Dodsworth, D. D.; Pekerar, S. V.; Requis, R.; Fiedler, P.; Garbarino, J. A.; Piovano, M. Rev. Latinoam. Quim. 1985, 16, 37. For approaches to the chiral synthesis of α-substituted serines; (a) Groth, U.; Chiang, Y-C.; Schollkopf, U. Liebigs Ann. Chem. 1982, 1756. (b) Seebach, D.; Aebi, J. D.; Gander- Coquoz, M.; Naef, R. Helv. Chim. Acta 1987, 70, 1194. (c) Ito, Y.; Sawamura, M.; Shirakawa, E.; Hayashizaki, K.; Hayashi, T. Tetrahedron Lett. 1988, 29, 235.
17. For the synthesis of racemic-α-substituted serines; (a) Calcagni, A.; Rossi, D.; Lucente, G. Synthesis 1981, 445. (b) Kaminski, Z. J.; Leplawy, M. T.; Zabrocki, J. Synthesis 1973, 792. (c) Dodsworth, D. D.; Pekerar, S. V.; Requis, R.; Fiedler, P.; Garbarino, J. A.; Piovano, M. Rev. Latinoam. Quim. 1985, 16, 37. For approaches to the chiral synthesis of α-substituted serines; (a) Groth, U.; Chiang, Y-C.; Schollkopf, U. Liebigs Ann. Chem. 1982, 1756. (b) Seebach, D.; Aebi, J. D.; Gander- Coquoz, M.; Naef, R. Helv. Chim. Acta 1987, 70, 1194. (c) Ito, Y.; Sawamura, M.; Shirakawa, E.; Hayashizaki, K.; Hayashi, T. Tetrahedron Lett. 1988, 29, 235.
18. For the synthesis of racemic-α-substituted serines; (a) Calcagni, A.; Rossi, D.; Lucente, G. Synthesis 1981, 445. (b) Kaminski, Z. J.; Leplawy, M. T.; Zabrocki, J. Synthesis 1973, 792. (c) Dodsworth, D. D.; Pekerar, S. V.; Requis, R.; Fiedler, P.; Garbarino, J. A.; Piovano, M. Rev. Latinoam. Quim. 1985, 16, 37. For approaches to the chiral synthesis of α-substituted serines; (a) Groth, U.; Chiang, Y-C.; Schollkopf, U. Liebigs Ann. Chem. 1982, 1756. (b) Seebach, D.; Aebi, J. D.; Gander- Coquoz, M.; Naef, R. Helv. Chim. Acta 1987, 70, 1194. (c) Ito, Y.; Sawamura, M.; Shirakawa, E.; Hayashizaki, K.; Hayashi, T. Tetrahedron Lett. 1988, 29, 235.
19. For the synthesis of racemic-α-substituted serines; (a) Calcagni, A.; Rossi, D.; Lucente, G. Synthesis 1981, 445. (b) Kaminski, Z. J.; Leplawy, M. T.; Zabrocki, J. Synthesis 1973, 792. (c) Dodsworth, D. D.; Pekerar, S. V.; Requis, R.; Fiedler, P.; Garbarino, J. A.; Piovano, M. Rev. Latinoam. Quim. 1985, 16, 37. For approaches to the chiral synthesis of α-substituted serines; (a) Groth, U.; Chiang, Y-C.; Schollkopf, U. Liebigs Ann. Chem. 1982, 1756. (b) Seebach, D.; Aebi, J. D.; Gander- Coquoz, M.; Naef, R. Helv. Chim. Acta 1987, 70, 1194. (c) Ito, Y.; Sawamura, M.; Shirakawa, E.; Hayashizaki, K.; Hayashi, T. Tetrahedron Lett. 1988, 29, 235.
20. Kulasegaram, S.; Kulawiec, R. J. J. Org. Chem. 1994, 59, 7195.
21. 3) δ 0.94 (3 H, d, J = 6.8 Hz), 0.98 (3 H, d, J = 6.8 Hz), 1.87 (1 H, brs), 2.40 (1 H, dsept, J = 2.8, 6.8 Hz), 2.90 (1 H, d, J = 13.6 Hz), 3.09 (1 H, d, J = 13.6 Hz), 3.76 (1 H, dd, J = 2.8, 4.4 Hz), 4.23 (1 H, d, J = 10.8 Hz), 4.37 (1 H, dd, J = 3.6, 10.8 Hz), 7.35 (2 H, brd, J = 6.0 Hz), 7.42 (3 H, m).
22. 13CN were observed. (Matrix Presented)
23. 2O) δ 2.95 (1 H, d, J = 14.0 Hz), 3.25 (1 H, d, J = 14.0 Hz), 3.77 (1 H, d, J = 12.0 Hz), 4.04 (1 H, d, J = 12.0 Hz), 7.26 (2 H, brd, J = 7.6 Hz), 7.4 (3H, m).
24. Shimamoto, K.; Ohfune, Y. J. Med. Chem. 1996, 39, 407.
25. 2O) δ 2.61 (1 H, d, J = 17.2 Hz), 2.79 (1 H, d, J = 17.2 Hz), 3.75 (1 H, d, J = 12.4 Hz), 3.88 (1 H, d, J = 12.4 Hz).
26. 2O).