Enantioselective solid-phase synthesis of α-amino acid derivatives

Tetrahedron

Volumn 55, Issue 20, 1999, Pages 6347-6362

  O'Donnell, Martin J ^a   Delgado, Francisca ^a   Pottorf, Richard S ^a  

^a INDIANA UNIVERSITY   (United States)

Author keywords

Amino acids and derivatives; Enantiocontrol; Phase transfer; Solid phase synthesis

Indexed keywords

ALPHA AMINO ACID; CINCHONIDINE; CINCHONINE; GLYCINE; QUATERNARY AMMONIUM DERIVATIVE; SCHIFF BASE;

ALKYLATION; AMINO ACID SYNTHESIS; ARTICLE; CATALYSIS; ENANTIOMER; PHASE TRANSITION; PRIORITY JOURNAL; TRANSAMINATION;

EID: 0033553459     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00211-2     Document Type: Article

References (77)

1. 1. O'Donnell, M. J.; Esikova, I. A.; Mi, A.; Shullenberger, D. F.; Wu, S. "Amino Acid and Peptide Synthesis Using Phase-Transfer Catalysis," in Phase-Transfer Catalysis: Mechanisms and Synthesis (ACS Symposium Series 659), Halpern, M. E., Ed., ACS: Washington, D. C., 1997, Chap. 10.
2. 2. For the preparation of racemic α-amino acids by PTC, see: (a) O'Donnell, M. J.; Boniece, J. M.; Earp, S. E. Tetrahedron Lett. 1978, 2641-2644. (b) O'Donnell, M. J.; Eckrich, T. M. Tetrahedron Lett. 1978, 4625-4628. (c) Ghosez, L.; Antoine, J. -P.; Deffense, E.; Navarro, M.; Libert, V.; O'Donnell, M. J.; Bruder, W. A.; Willey, K.; Wojciechowski, K. Tetrahedron Lett. 1982, 23, 4255-4258. (d) O'Donnell, M. J.; Bruder, W. A.; Eckrich, T. M.; Shullenberger, D. F.; Staten, G. S. Synthesis 1984, 127-128. (e) O'Donnell, M. J.; Wojciechowski, K. Synthesis 1984, 313-315. (e) O'Donnell, M. J.; Wojciechowski, K. Synthesis 1984, 313-315. (f) O'Donnell, M. J.; Barney, C. L.; McCarthy, J. R. Tetrahedron Lett. 1985, 26, 3067-3070. (g) McCarthy, J. R.; Barney, C. L.; O'Donnell, M. J.; Huffman, J. C. Chem. Commun. 1987, 469-470.
3. 2. For the preparation of racemic α-amino acids by PTC, see: (a) O'Donnell, M. J.; Boniece, J. M.; Earp, S. E. Tetrahedron Lett. 1978, 2641-2644. (b) O'Donnell, M. J.; Eckrich, T. M. Tetrahedron Lett. 1978, 4625-4628. (c) Ghosez, L.; Antoine, J. -P.; Deffense, E.; Navarro, M.; Libert, V.; O'Donnell, M. J.; Bruder, W. A.; Willey, K.; Wojciechowski, K. Tetrahedron Lett. 1982, 23, 4255-4258. (d) O'Donnell, M. J.; Bruder, W. A.; Eckrich, T. M.; Shullenberger, D. F.; Staten, G. S. Synthesis 1984, 127-128. (e) O'Donnell, M. J.; Wojciechowski, K. Synthesis 1984, 313-315. (e) O'Donnell, M. J.; Wojciechowski, K. Synthesis 1984, 313-315. (f) O'Donnell, M. J.; Barney, C. L.; McCarthy, J. R. Tetrahedron Lett. 1985, 26, 3067-3070. (g) McCarthy, J. R.; Barney, C. L.; O'Donnell, M. J.; Huffman, J. C. Chem. Commun. 1987, 469-470.
4. 2. For the preparation of racemic α-amino acids by PTC, see: (a) O'Donnell, M. J.; Boniece, J. M.; Earp, S. E. Tetrahedron Lett. 1978, 2641-2644. (b) O'Donnell, M. J.; Eckrich, T. M. Tetrahedron Lett. 1978, 4625-4628. (c) Ghosez, L.; Antoine, J. -P.; Deffense, E.; Navarro, M.; Libert, V.; O'Donnell, M. J.; Bruder, W. A.; Willey, K.; Wojciechowski, K. Tetrahedron Lett. 1982, 23, 4255-4258. (d) O'Donnell, M. J.; Bruder, W. A.; Eckrich, T. M.; Shullenberger, D. F.; Staten, G. S. Synthesis 1984, 127-128. (e) O'Donnell, M. J.; Wojciechowski, K. Synthesis 1984, 313-315. (e) O'Donnell, M. J.; Wojciechowski, K. Synthesis 1984, 313-315. (f) O'Donnell, M. J.; Barney, C. L.; McCarthy, J. R. Tetrahedron Lett. 1985, 26, 3067-3070. (g) McCarthy, J. R.; Barney, C. L.; O'Donnell, M. J.; Huffman, J. C. Chem. Commun. 1987, 469-470.
5. 2. For the preparation of racemic α-amino acids by PTC, see: (a) O'Donnell, M. J.; Boniece, J. M.; Earp, S. E. Tetrahedron Lett. 1978, 2641-2644. (b) O'Donnell, M. J.; Eckrich, T. M. Tetrahedron Lett. 1978, 4625-4628. (c) Ghosez, L.; Antoine, J. -P.; Deffense, E.; Navarro, M.; Libert, V.; O'Donnell, M. J.; Bruder, W. A.; Willey, K.; Wojciechowski, K. Tetrahedron Lett. 1982, 23, 4255-4258. (d) O'Donnell, M. J.; Bruder, W. A.; Eckrich, T. M.; Shullenberger, D. F.; Staten, G. S. Synthesis 1984, 127-128. (e) O'Donnell, M. J.; Wojciechowski, K. Synthesis 1984, 313-315. (e) O'Donnell, M. J.; Wojciechowski, K. Synthesis 1984, 313-315. (f) O'Donnell, M. J.; Barney, C. L.; McCarthy, J. R. Tetrahedron Lett. 1985, 26, 3067-3070. (g) McCarthy, J. R.; Barney, C. L.; O'Donnell, M. J.; Huffman, J. C. Chem. Commun. 1987, 469-470.
6. 2. For the preparation of racemic α-amino acids by PTC, see: (a) O'Donnell, M. J.; Boniece, J. M.; Earp, S. E. Tetrahedron Lett. 1978, 2641-2644. (b) O'Donnell, M. J.; Eckrich, T. M. Tetrahedron Lett. 1978, 4625-4628. (c) Ghosez, L.; Antoine, J. -P.; Deffense, E.; Navarro, M.; Libert, V.; O'Donnell, M. J.; Bruder, W. A.; Willey, K.; Wojciechowski, K. Tetrahedron Lett. 1982, 23, 4255-4258. (d) O'Donnell, M. J.; Bruder, W. A.; Eckrich, T. M.; Shullenberger, D. F.; Staten, G. S. Synthesis 1984, 127-128. (e) O'Donnell, M. J.; Wojciechowski, K. Synthesis 1984, 313-315. (e) O'Donnell, M. J.; Wojciechowski, K. Synthesis 1984, 313-315. (f) O'Donnell, M. J.; Barney, C. L.; McCarthy, J. R. Tetrahedron Lett. 1985, 26, 3067-3070. (g) McCarthy, J. R.; Barney, C. L.; O'Donnell, M. J.; Huffman, J. C. Chem. Commun. 1987, 469-470.
7. 2. For the preparation of racemic α-amino acids by PTC, see: (a) O'Donnell, M. J.; Boniece, J. M.; Earp, S. E. Tetrahedron Lett. 1978, 2641-2644. (b) O'Donnell, M. J.; Eckrich, T. M. Tetrahedron Lett. 1978, 4625-4628. (c) Ghosez, L.; Antoine, J. -P.; Deffense, E.; Navarro, M.; Libert, V.; O'Donnell, M. J.; Bruder, W. A.; Willey, K.; Wojciechowski, K. Tetrahedron Lett. 1982, 23, 4255-4258. (d) O'Donnell, M. J.; Bruder, W. A.; Eckrich, T. M.; Shullenberger, D. F.; Staten, G. S. Synthesis 1984, 127-128. (e) O'Donnell, M. J.; Wojciechowski, K. Synthesis 1984, 313-315. (e) O'Donnell, M. J.; Wojciechowski, K. Synthesis 1984, 313-315. (f) O'Donnell, M. J.; Barney, C. L.; McCarthy, J. R. Tetrahedron Lett. 1985, 26, 3067-3070. (g) McCarthy, J. R.; Barney, C. L.; O'Donnell, M. J.; Huffman, J. C. Chem. Commun. 1987, 469-470.
8. 2. For the preparation of racemic α-amino acids by PTC, see: (a) O'Donnell, M. J.; Boniece, J. M.; Earp, S. E. Tetrahedron Lett. 1978, 2641-2644. (b) O'Donnell, M. J.; Eckrich, T. M. Tetrahedron Lett. 1978, 4625-4628. (c) Ghosez, L.; Antoine, J. -P.; Deffense, E.; Navarro, M.; Libert, V.; O'Donnell, M. J.; Bruder, W. A.; Willey, K.; Wojciechowski, K. Tetrahedron Lett. 1982, 23, 4255-4258. (d) O'Donnell, M. J.; Bruder, W. A.; Eckrich, T. M.; Shullenberger, D. F.; Staten, G. S. Synthesis 1984, 127-128. (e) O'Donnell, M. J.; Wojciechowski, K. Synthesis 1984, 313-315. (e) O'Donnell, M. J.; Wojciechowski, K. Synthesis 1984, 313-315. (f) O'Donnell, M. J.; Barney, C. L.; McCarthy, J. R. Tetrahedron Lett. 1985, 26, 3067-3070. (g) McCarthy, J. R.; Barney, C. L.; O'Donnell, M. J.; Huffman, J. C. Chem. Commun. 1987, 469-470.
9. 2. For the preparation of racemic α-amino acids by PTC, see: (a) O'Donnell, M. J.; Boniece, J. M.; Earp, S. E. Tetrahedron Lett. 1978, 2641-2644. (b) O'Donnell, M. J.; Eckrich, T. M. Tetrahedron Lett. 1978, 4625-4628. (c) Ghosez, L.; Antoine, J. -P.; Deffense, E.; Navarro, M.; Libert, V.; O'Donnell, M. J.; Bruder, W. A.; Willey, K.; Wojciechowski, K. Tetrahedron Lett. 1982, 23, 4255-4258. (d) O'Donnell, M. J.; Bruder, W. A.; Eckrich, T. M.; Shullenberger, D. F.; Staten, G. S. Synthesis 1984, 127-128. (e) O'Donnell, M. J.; Wojciechowski, K. Synthesis 1984, 313-315. (e) O'Donnell, M. J.; Wojciechowski, K. Synthesis 1984, 313-315. (f) O'Donnell, M. J.; Barney, C. L.; McCarthy, J. R. Tetrahedron Lett. 1985, 26, 3067-3070. (g) McCarthy, J. R.; Barney, C. L.; O'Donnell, M. J.; Huffman, J. C. Chem. Commun. 1987, 469-470.
10. 3. For the preparation of racemic α,α-dialkylamino acids by PTC, typically via aldimine derivatives, see: (a) O'Donnell, M. J.; LeClef, B.; Rusterholz, D. B.; Ghosez, L.; Antoine, J. -P.; Navarro, M. Tetrahedron Lett. 1982, 23, 4259-4262. (b) Reference 2d. (c) Reference 2e. (d) O'Donnell, M. J.; Rusterholz, D. B. Synth. Commun. 1989, 19, 1157-1165.
11. 3. For the preparation of racemic α,α-dialkylamino acids by PTC, typically via aldimine derivatives, see: (a) O'Donnell, M. J.; LeClef, B.; Rusterholz, D. B.; Ghosez, L.; Antoine, J. -P.; Navarro, M. Tetrahedron Lett. 1982, 23, 4259-4262. (b) Reference 2d. (c) Reference 2e. (d) O'Donnell, M. J.; Rusterholz, D. B. Synth. Commun. 1989, 19, 1157-1165.
12. 3. For the preparation of racemic α,α-dialkylamino acids by PTC, typically via aldimine derivatives, see: (a) O'Donnell, M. J.; LeClef, B.; Rusterholz, D. B.; Ghosez, L.; Antoine, J. -P.; Navarro, M. Tetrahedron Lett. 1982, 23, 4259-4262. (b) Reference 2d. (c) Reference 2e. (d) O'Donnell, M. J.; Rusterholz, D. B. Synth. Commun. 1989, 19, 1157-1165.
13. 3. For the preparation of racemic α,α-dialkylamino acids by PTC, typically via aldimine derivatives, see: (a) O'Donnell, M. J.; LeClef, B.; Rusterholz, D. B.; Ghosez, L.; Antoine, J. -P.; Navarro, M. Tetrahedron Lett. 1982, 23, 4259-4262. (b) Reference 2d. (c) Reference 2e. (d) O'Donnell, M. J.; Rusterholz, D. B. Synth. Commun. 1989, 19, 1157-1165.
14. 4. O'Donnell, M. J.; Bennett, W. D.; Bruder, W. A.; Jacobsen, W. N.; Knuth, K.; LeClef, B.; Polt, R. L.; Bordwell, F. G.; Mrozack, S. R.; Cripe, T. A. J. Am. Chem. Soc. 1988, 110, 8520-8525.
15. 5. O'Donnell, M. J.; Polt, R. L. J. Org. Chem. 1982, 47, 2663-2666.
16. 6. For recent α-amino acid syntheses involving chiral auxiliaries in conjunction with Schiff base-type derivatives, see: (a) López, A.; Pleixats, R. Tetrahedron: Asymm. 1998, 9, 1967-1977. (b) Chinchilla, R.; Galindo, N.; Nájera, C. Tetrahedron: Asymm. 1998, 9, 2769-2772. (c) Meyer, L. Poirier, J. -M.; Duhamel, P.; Duhamel, L. J. Org. Chem. 1998, 63, 8094-8095.
17. 6. For recent α-amino acid syntheses involving chiral auxiliaries in conjunction with Schiff base-type derivatives, see: (a) López, A.; Pleixats, R. Tetrahedron: Asymm. 1998, 9, 1967-1977. (b) Chinchilla, R.; Galindo, N.; Nájera, C. Tetrahedron: Asymm. 1998, 9, 2769-2772. (c) Meyer, L. Poirier, J. -M.; Duhamel, P.; Duhamel, L. J. Org. Chem. 1998, 63, 8094-8095.
18. 6. For recent α-amino acid syntheses involving chiral auxiliaries in conjunction with Schiff base-type derivatives, see: (a) López, A.; Pleixats, R. Tetrahedron: Asymm. 1998, 9, 1967-1977. (b) Chinchilla, R.; Galindo, N.; Nájera, C. Tetrahedron: Asymm. 1998, 9, 2769-2772. (c) Meyer, L. Poirier, J. -M.; Duhamel, P.; Duhamel, L. J. Org. Chem. 1998, 63, 8094-8095.
19. 7. (a) O'Donnell, M. J. "Asymmetric Phase Transfer Reactions," in Catalytic Asymmetric Synthesis, Ojima, I., Ed., Verlag Chemie: New York, 1993, Chap. 8. (b) Shioiri, T. "Chiral Phase Transfer Catalysis," in Handbook of Phase Transfer Catalysis, Sasson, Y. and Neumann, R., Eds., Blackie Academic &Professional: London, 1997, Chap. 14.
20. 7. (a) O'Donnell, M. J. "Asymmetric Phase Transfer Reactions," in Catalytic Asymmetric Synthesis, Ojima, I., Ed., Verlag Chemie: New York, 1993, Chap. 8. (b) Shioiri, T. "Chiral Phase Transfer Catalysis," in Handbook of Phase Transfer Catalysis, Sasson, Y. and Neumann, R., Eds., Blackie Academic & Professional: London, 1997, Chap. 14.
21. 8. For a recent short review on the preparation of amino acids by asymmetric PTC reactions, see: O'Donnell, M. J. Phases 1998, Issue 4, 5-8 (Phases is a PTC newsletter published by SACHEM, Inc. 821 E. Woodward, Austin, TX 78704).
22. 9. O'Donnell, M. J.; Bennett, W. D.; Wu, S. J. Am. Chem. Soc. 1989, 111, 2353-2355.
23. 10. For a related catalytic enantioselective synthesis of α,α-dialkylated amino acid derivatives by PTC using aldimine derivatives, see: O'Donnell, M. J.; Wu, S. Tetrahedron: Asymm. 1992, 3, 591-594.
24. 11. Dolling, U. -H.; Davis, P.; Grabowski, E. J. J. J. Am. Chem. Soc. 1984, 106, 446-447.
25. 12. For other chiral PTC alkylations of 1b followed by recrystallization to give products of higher optical purity, see: (a) Tohdo, K.; Hamada, Y.; Shioiri, T. Peptide Chem. 1992, 29, 7-12. (b) Imperiali, B.; Fisher, S. L. J. Org. Chem. 1992, 57, 757-759. (c) Tohdo, K.; Hamada, Y.; Shioiri, T. SYNLETT 1994, 247-249. (d) Imperiali, B.; Roy, R. S. J. Org. Chem. 1995, 60, 1891-1894. (e) Torrado, A.; Imperiali, B. J. Org. Chem. 1996, 61, 8940-8948. 13. (a) Imperiali, B.; Prins, T. J.; Fisher, S. L. J. Org. Chem. 1993, 58, 1613-1616. (b) Reference 12e.
26. 12. For other chiral PTC alkylations of 1b followed by recrystallization to give products of higher optical purity, see: (a) Tohdo, K.; Hamada, Y.; Shioiri, T. Peptide Chem. 1992, 29, 7-12. (b) Imperiali, B.; Fisher, S. L. J. Org. Chem. 1992, 57, 757-759. (c) Tohdo, K.; Hamada, Y.; Shioiri, T. SYNLETT 1994, 247-249. (d) Imperiali, B.; Roy, R. S. J. Org. Chem. 1995, 60, 1891-1894. (e) Torrado, A.; Imperiali, B. J. Org. Chem. 1996, 61, 8940-8948. 13. (a) Imperiali, B.; Prins, T. J.; Fisher, S. L. J. Org. Chem. 1993, 58, 1613-1616. (b) Reference 12e.
27. 12. For other chiral PTC alkylations of 1b followed by recrystallization to give products of higher optical purity, see: (a) Tohdo, K.; Hamada, Y.; Shioiri, T. Peptide Chem. 1992, 29, 7-12. (b) Imperiali, B.; Fisher, S. L. J. Org. Chem. 1992, 57, 757-759. (c) Tohdo, K.; Hamada, Y.; Shioiri, T. SYNLETT 1994, 247-249. (d) Imperiali, B.; Roy, R. S. J. Org. Chem. 1995, 60, 1891-1894. (e) Torrado, A.; Imperiali, B. J. Org. Chem. 1996, 61, 8940-8948. 13. (a) Imperiali, B.; Prins, T. J.; Fisher, S. L. J. Org. Chem. 1993, 58, 1613-1616. (b) Reference 12e.
28. 12. For other chiral PTC alkylations of 1b followed by recrystallization to give products of higher optical purity, see: (a) Tohdo, K.; Hamada, Y.; Shioiri, T. Peptide Chem. 1992, 29, 7-12. (b) Imperiali, B.; Fisher, S. L. J. Org. Chem. 1992, 57, 757-759. (c) Tohdo, K.; Hamada, Y.; Shioiri, T. SYNLETT 1994, 247-249. (d) Imperiali, B.; Roy, R. S. J. Org. Chem. 1995, 60, 1891-1894. (e) Torrado, A.; Imperiali, B. J. Org. Chem. 1996, 61, 8940-8948. 13. (a) Imperiali, B.; Prins, T. J.; Fisher, S. L. J. Org. Chem. 1993, 58, 1613-1616. (b) Reference 12e.
29. 12. For other chiral PTC alkylations of 1b followed by recrystallization to give products of higher optical purity, see: (a) Tohdo, K.; Hamada, Y.; Shioiri, T. Peptide Chem. 1992, 29, 7-12. (b) Imperiali, B.; Fisher, S. L. J. Org. Chem. 1992, 57, 757-759. (c) Tohdo, K.; Hamada, Y.; Shioiri, T. SYNLETT 1994, 247-249. (d) Imperiali, B.; Roy, R. S. J. Org. Chem. 1995, 60, 1891-1894. (e) Torrado, A.; Imperiali, B. J. Org. Chem. 1996, 61, 8940-8948. 13. (a) Imperiali, B.; Prins, T. J.; Fisher, S. L. J. Org. Chem. 1993, 58, 1613-1616. (b) Reference 12e.
30. 13. (a) Imperiali, B.; Prins, T. J.; Fisher, S. L. J. Org. Chem. 1993, 58, 1613-1616. (b) Reference 12e.
31. 14. A caution has been noted for chiral PTC alkylations involving alkyl halides that can be easily reduced. Attempted alkylation of 1 with (bromomethyl)cyclooctatetraene using a chiral cinchona-derived catalyst gave only racemic product. See: Pirrung, M. C.; Krishnamurthy, N. J. Org. Chem. 1993, 58, 954-956.
32. 15. (a) O'Donnell, M. J.; Wu, S.; Huffman, J. C. Tetrahedron 1994, 50, 4507-4518. (b) O'Donnell, M. J.; Wu, S.; Esikova, I.; Mi, A. U.S. Patent, 1996, 5,554,753.
33. 15. (a) O'Donnell, M. J.; Wu, S.; Huffman, J. C. Tetrahedron 1994, 50, 4507-4518. (b) O'Donnell, M. J.; Wu, S.; Esikova, I.; Mi, A. U.S. Patent, 1996, 5,554,753.
34. 16. Esikova, I. A.; Nahreini, T. S.; O'Donnell, M. J. "A New Interfacial Mechanism for Asymmetric Alkylation by Phase-Transfer Catalysis," in Phase-Transfer Catalysis: Mechanisms and Synthesis (ACS Symposium Series 659), Halpern, M. E., Ed., ACS: Washington, D. C., 1997, Chap. 7.
35. 17. Lygo, B.; Wainwright, P. G. Tetrahedron Lett. 1997, 38, 8595-8598.
36. 18. (a) Corey, E. J.; Xu, F.; Noe, M. C. J. Am. Chem. Soc. 1997, 119, 12414-12415. (b) Corey, E. J.; Noe, M. C.; Xu, F. Tetrahedron Lett. 1998, 39, 5347-5350.
37. 18. (a) Corey, E. J.; Xu, F.; Noe, M. C. J. Am. Chem. Soc. 1997, 119, 12414-12415.
38. 19. For solution-phase precedence for the selective PTC alkylation of dipeptides, see: O'Donnell, M. J.; Burkholder, T. P.; Khau, V. V.; Roeske, R. W.; Tian, Z. Polish J. Chem. 1994, 68, 2477-2488.
39. 20. (a) O'Donnell, M. J.; Zhou, C.; Scott, W. L. J. Am. Chem. Soc. 1996, 118, 6070-6071. (b) O'Donnell, M. J.; Lugar, C. W.; Pottorf, R. S.; Zhou, C.; Scott, W. L.; Cwi, C. L. Tetrahedron Lett. 1997, 38, 7163-7166.
40. 20. (a) O'Donnell, M. J.; Zhou, C.; Scott, W. L. J. Am. Chem. Soc. 1996, 118, 6070-6071. (b) O'Donnell, M. J.; Lugar, C. W.; Pottorf, R. S.; Zhou, C.; Scott, W. L.; Cwi, C. L. Tetrahedron Lett. 1997, 38, 7163-7166.
41. 21. For recent solution-phase C-alkylations of peptides, see: (a) Miyashita, K.; Iwaki, H.; Tai, K.; Murafuji, H.; Imanishi, T. Chem. Commun. 1998, 1987-1988 (stereoselective N-terminal α-alkylation using a pyridoxal imine model). (b) Matt, T.; Seebach, D. Helv. Chim. Acta 1998, 81, 1845-1895 (alkylation at aminomalonate-and (amino)(cyano)acetate-containing residues).
42. 21. For recent solution-phase C-alkylations of peptides, see: (a) Miyashita, K.; Iwaki, H.; Tai, K.; Murafuji, H.; Imanishi, T. Chem. Commun. 1998, 1987-1988 (stereoselective N-terminal α-alkylation using a pyridoxal imine model). (b) Matt, T.; Seebach, D. Helv. Chim. Acta 1998, 81, 1845-1895 (alkylation at aminomalonate-and (amino)(cyano)acetate-containing residues).
43. 22. For a PTC alkylation route using a soluble polymer support (PEG) in combination with Schiff base ester methodology, see: Sauvagnat, B.; Lamaty, F.; Lazaro, R.; Martinez, J. Tetrahedron Lett. 1998, 39, 821-824.
44. 23. For a recent solid-phase synthesis of α-amino acid derivatives by Michael addition to a resin-bound dehydroalanine, see: Barbaste, M.; Rolland-Fulcrand, V.; Roumestant, M. -L.; Viallefont, P.; Martinez, J. Tetrahedron Lett. 1998, 39, 6287-6290.
45. 24. For selected recent reviews about solid-phase synthesis, see: (a) James, I. W. Mol. Diversity 1997, 2, 175-180; Mol. Diversity 1998, 3, 181-190. (b) Brown, A. R.; Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. SYNLETT 1998, 817-827. (c) Brown, R. C. D. J. Chem. Soc., Perkin Trans 1 1998, 3293-3320.
46. 24. For selected recent reviews about solid-phase synthesis, see: (a) James, I. W. Mol. Diversity 1997, 2, 175-180; Mol. Diversity 1998, 3, 181-190. (b) Brown, A. R.; Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. SYNLETT 1998, 817-827. (c) Brown, R. C. D. J. Chem. Soc., Perkin Trans 1 1998, 3293-3320.
47. 24. For selected recent reviews about solid-phase synthesis, see: (a) James, I. W. Mol. Diversity 1997, 2, 175-180; Mol. Diversity 1998, 3, 181-190. (b) Brown, A. R.; Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. SYNLETT 1998, 817-827. (c) Brown, R. C. D. J. Chem. Soc., Perkin Trans 1 1998, 3293-3320.
48. 24. For selected recent reviews about solid-phase synthesis, see: (a) James, I. W. Mol. Diversity 1997, 2, 175-180; Mol. Diversity 1998, 3, 181-190. (b) Brown, A. R.; Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. SYNLETT 1998, 817-827. (c) Brown, R. C. D. J. Chem. Soc., Perkin Trans 1 1998, 3293-3320.
49. 25. For selected recent reviews and books about combinatorial chemistry, see: (a) "Applications of Solid-Supported Organic Synthesis in Combinatorial Chemistry," Bristol, J. A. (Ed.), Tetrahedron Symposium-in-Print, Tetrahedron 1997, 53, Issue 19, pages 6573-6705. (b) A Practical Guide to Combinatorial Chemistry; Czarnik. A. W.; DeWitt, S. H. (Eds.); American Chemical Society: Washington, D. C., 1997. (c) Annual Reports in Combinatorial Chemistry and Molecular Diversity, Volume 1; Moos, W. H.; Pavia, M. R.; Kay, B. K.; Ellington, A. D. (Eds.); ESCOM: Leiden, Netherlands, 1997. (d) Wilson, S.; Czarnik, A. W. Combinatorial Chemistry: Synthesis and Applications; Wiley: New York, 1997. (e) Bunin, B. A. The Combinatorial Index; Academic Press: San Diego, California, 1998. (f) Combinatorial Chemistry and Molecular Diversity in Drug Discovery; Gordon, E. M.; Kerwin, J. F., Jr. (Eds.); Wiley-Liss: New York, 1998. (g) Terrett, N. K. Combinatorial Chemistry; Oxford University Press: Oxford, 1998.
50. 25. For selected recent reviews and books about combinatorial chemistry, see: (a) "Applications of Solid-Supported Organic Synthesis in Combinatorial Chemistry," Bristol, J. A. (Ed.), Tetrahedron Symposium-in-Print, Tetrahedron 1997, 53, Issue 19, pages 6573-6705. (b) A Practical Guide to Combinatorial Chemistry; Czarnik. A. W.; DeWitt, S. H. (Eds.); American Chemical Society: Washington, D. C., 1997. (c) Annual Reports in Combinatorial Chemistry and Molecular Diversity, Volume 1; Moos, W. H.; Pavia, M. R.; Kay, B. K.; Ellington, A. D. (Eds.); ESCOM: Leiden, Netherlands, 1997. (d) Wilson, S.; Czarnik, A. W. Combinatorial Chemistry: Synthesis and Applications; Wiley: New York, 1997. (e) Bunin, B. A. The Combinatorial Index; Academic Press: San Diego, California, 1998. (f) Combinatorial Chemistry and Molecular Diversity in Drug Discovery; Gordon, E. M.; Kerwin, J. F., Jr. (Eds.); Wiley-Liss: New York, 1998. (g) Terrett, N. K. Combinatorial Chemistry; Oxford University Press: Oxford, 1998.
51. 25. For selected recent reviews and books about combinatorial chemistry, see: (a) "Applications of Solid-Supported Organic Synthesis in Combinatorial Chemistry," Bristol, J. A. (Ed.), Tetrahedron Symposium-in-Print, Tetrahedron 1997, 53, Issue 19, pages 6573-6705. (b) A Practical Guide to Combinatorial Chemistry; Czarnik. A. W.; DeWitt, S. H. (Eds.); American Chemical Society: Washington, D. C., 1997. (c) Annual Reports in Combinatorial Chemistry and Molecular Diversity, Volume 1; Moos, W. H.; Pavia, M. R.; Kay, B. K.; Ellington, A. D. (Eds.); ESCOM: Leiden, Netherlands, 1997. (d) Wilson, S.; Czarnik, A. W. Combinatorial Chemistry: Synthesis and Applications; Wiley: New York, 1997. (e) Bunin, B. A. The Combinatorial Index; Academic Press: San Diego, California, 1998. (f) Combinatorial Chemistry and Molecular Diversity in Drug Discovery; Gordon, E. M.; Kerwin, J. F., Jr. (Eds.); Wiley-Liss: New York, 1998. (g) Terrett, N. K. Combinatorial Chemistry; Oxford University Press: Oxford, 1998.
52. 25. For selected recent reviews and books about combinatorial chemistry, see: (a) "Applications of Solid-Supported Organic Synthesis in Combinatorial Chemistry," Bristol, J. A. (Ed.), Tetrahedron Symposium-in-Print, Tetrahedron 1997, 53, Issue 19, pages 6573-6705. (b) A Practical Guide to Combinatorial Chemistry; Czarnik. A. W.; DeWitt, S. H. (Eds.); American Chemical Society: Washington, D. C., 1997. (c) Annual Reports in Combinatorial Chemistry and Molecular Diversity, Volume 1; Moos, W. H.; Pavia, M. R.; Kay, B. K.; Ellington, A. D. (Eds.); ESCOM: Leiden, Netherlands, 1997. (d) Wilson, S.; Czarnik, A. W. Combinatorial Chemistry: Synthesis and Applications; Wiley: New York, 1997. (e) Bunin, B. A. The Combinatorial Index; Academic Press: San Diego, California, 1998. (f) Combinatorial Chemistry and Molecular Diversity in Drug Discovery; Gordon, E. M.; Kerwin, J. F., Jr. (Eds.); Wiley-Liss: New York, 1998. (g) Terrett, N. K. Combinatorial Chemistry; Oxford University Press: Oxford, 1998.
53. 25. For selected recent reviews and books about combinatorial chemistry, see: (a) "Applications of Solid-Supported Organic Synthesis in Combinatorial Chemistry," Bristol, J. A. (Ed.), Tetrahedron Symposium-in-Print, Tetrahedron 1997, 53, Issue 19, pages 6573-6705. (b) A Practical Guide to Combinatorial Chemistry; Czarnik. A. W.; DeWitt, S. H. (Eds.); American Chemical Society: Washington, D. C., 1997. (c) Annual Reports in Combinatorial Chemistry and Molecular Diversity, Volume 1; Moos, W. H.; Pavia, M. R.; Kay, B. K.; Ellington, A. D. (Eds.); ESCOM: Leiden, Netherlands, 1997. (d) Wilson, S.; Czarnik, A. W. Combinatorial Chemistry: Synthesis and Applications; Wiley: New York, 1997. (e) Bunin, B. A. The Combinatorial Index; Academic Press: San Diego, California, 1998. (f) Combinatorial Chemistry and Molecular Diversity in Drug Discovery; Gordon, E. M.; Kerwin, J. F., Jr. (Eds.); Wiley-Liss: New York, 1998. (g) Terrett, N. K. Combinatorial Chemistry; Oxford University Press: Oxford, 1998.
54. 25. For selected recent reviews and books about combinatorial chemistry, see: (a) "Applications of Solid-Supported Organic Synthesis in Combinatorial Chemistry," Bristol, J. A. (Ed.), Tetrahedron Symposium-in-Print, Tetrahedron 1997, 53, Issue 19, pages 6573-6705. (b) A Practical Guide to Combinatorial Chemistry; Czarnik. A. W.; DeWitt, S. H. (Eds.); American Chemical Society: Washington, D. C., 1997. (c) Annual Reports in Combinatorial Chemistry and Molecular Diversity, Volume 1; Moos, W. H.; Pavia, M. R.; Kay, B. K.; Ellington, A. D. (Eds.); ESCOM: Leiden, Netherlands, 1997. (d) Wilson, S.; Czarnik, A. W. Combinatorial Chemistry: Synthesis and Applications; Wiley: New York, 1997. (e) Bunin, B. A. The Combinatorial Index; Academic Press: San Diego, California, 1998. (f) Combinatorial Chemistry and Molecular Diversity in Drug Discovery; Gordon, E. M.; Kerwin, J. F., Jr. (Eds.); Wiley-Liss: New York, 1998. (g) Terrett, N. K. Combinatorial Chemistry; Oxford University Press: Oxford, 1998.
55. 25. For selected recent reviews and books about combinatorial chemistry, see: (a) "Applications of Solid-Supported Organic Synthesis in Combinatorial Chemistry," Bristol, J. A. (Ed.), Tetrahedron Symposium-in-Print, Tetrahedron 1997, 53, Issue 19, pages 6573-6705. (b) A Practical Guide to Combinatorial Chemistry; Czarnik. A. W.; DeWitt, S. H. (Eds.); American Chemical Society: Washington, D. C., 1997. (c) Annual Reports in Combinatorial Chemistry and Molecular Diversity, Volume 1; Moos, W. H.; Pavia, M. R.; Kay, B. K.; Ellington, A. D. (Eds.); ESCOM: Leiden, Netherlands, 1997. (d) Wilson, S.; Czarnik, A. W. Combinatorial Chemistry: Synthesis and Applications; Wiley: New York, 1997. (e) Bunin, B. A. The Combinatorial Index; Academic Press: San Diego, California, 1998. (f) Combinatorial Chemistry and Molecular Diversity in Drug Discovery; Gordon, E. M.; Kerwin, J. F., Jr. (Eds.); Wiley-Liss: New York, 1998. (g) Terrett, N. K. Combinatorial Chemistry; Oxford University Press: Oxford, 1998.
56. 26. (a) Solid-Phase Peptide Synthesis; Fields, G. B. (Ed.), Methods in Enzymology, Vol. 289; Academic Press: San Diego, California, 1997. (b) Hruby, V. J.; Meyer, J. -P. In Bioorg. Chem.: Pept. Proteins; Hecht, S. M. (Ed.); Oxford University Press: New York, 1998, pp 27-64, 473-479. (c.)Al-Obeidi, F.; Hruby, V. J.; Sawyer, T. K. Mol. Biotechnol. 1998, 9, 205-223.
57. 26. (a) Solid-Phase Peptide Synthesis; Fields, G. B. (Ed.), Methods in Enzymology, Vol. 289; Academic Press: San Diego, California, 1997. (b) Hruby, V. J.; Meyer, J. -P. In Bioorg. Chem.: Pept. Proteins; Hecht, S. M. (Ed.); Oxford University Press: New York, 1998, pp 27-64, 473-479. (c.)Al-Obeidi, F.; Hruby, V. J.; Sawyer, T. K. Mol. Biotechnol. 1998, 9, 205-223.
58. 26. (a) Solid-Phase Peptide Synthesis; Fields, G. B. (Ed.), Methods in Enzymology, Vol. 289; Academic Press: San Diego, California, 1997. (b) Hruby, V. J.; Meyer, J. -P. In Bioorg. Chem.: Pept. Proteins; Hecht, S. M. (Ed.); Oxford University Press: New York, 1998, pp 27-64, 473-479. (c.)Al-Obeidi, F.; Hruby, V. J.; Sawyer, T. K. Mol. Biotechnol. 1998, 9, 205-223.
59. 27. Abbreviations: BEMP = 2-t-butylimino-2-diethylamino-1,3-dimethylperhydro-1,3,2-diazaphosphorine; BTPP = t-butylimino-tri(pyrrolidino)phosphorane; KHMDS = potassium bis(trimethylsilyl)amide; NMP = 1-methyl-2-pyrrolidinone; DIEA = diisopropylethyl amine; HOBt = 1-hydroxybenzotriazole; DIC = diisopropyl carbodiimide; HATU = O-(7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate; TFA = trifluoroacetic acid.
60. 28. Scott, W. L.; Zhou, C.; Fang, Z.; O'Donnell, M. J. Tetrahedron Lett. 1997, 38, 3695-3698.
61. 29. Griffith, D. L.; O'Donnell, M. J.; Pottorf, R. S.; Scott, W. L.; Porco, J. A., Jr. Tetrahedron Lett. 1997, 38, 8821-8824.
62. 30. Domínguez, E.; O'Donnell, M. J.; Scott, W. L. Tetrahedron Lett., 1998, 39, 2167-2170.
63. 31. O'Donnell, M. J.; Delgado, F.; Hostettler, C.; Schwesinger, R. Tetrahedron Lett. 1998, 39, 8775-8778.
64. 32. As noted by Jacoben and coworkers, to date stereoselective reactions have played a relatively minor part in the rapidly growing area of solid-phase synthesis. For a discussion of the importance of developing such reactions, especially their enantioselective variants, see: Annis, D. A.; Helluin, O.; Jacobsen, E. N. Angew. Chem., Int. Ed. Engl. 1998, 37, 1907-1909 and cited references.
65. 33. (a) Nimura, N.; Ogura, H.; Kinoshita, T. J. Chromatogr. 1980, 202, 375-379. (b) Kinoshita, T.; Kasahara, Y.; Nimura, N. J. Chromatogr. 1981, 210, 77-81. (c) Nimura, N.; Toyama, A.; Kinoshita, T. J. Chromatogr. 1984, 316, 547-552.
66. 33. (a) Nimura, N.; Ogura, H.; Kinoshita, T. J. Chromatogr. 1980, 202, 375-379. (b) Kinoshita, T.; Kasahara, Y.; Nimura, N. J. Chromatogr. 1981, 210, 77-81. (c) Nimura, N.; Toyama, A.; Kinoshita, T. J. Chromatogr. 1984, 316, 547-552.
67. 33. (a) Nimura, N.; Ogura, H.; Kinoshita, T. J. Chromatogr. 1980, 202, 375-379. (b) Kinoshita, T.; Kasahara, Y.; Nimura, N. J. Chromatogr. 1981, 210, 77-81. (c) Nimura, N.; Toyama, A.; Kinoshita, T. J. Chromatogr. 1984, 316, 547-552.
68. 34. Péter, A.; Török, G., Tóth, G.; Van Den Nest, W.; Laus, G.; Tourwé, D. J. Chromatogr. A 1998, 797, 165-176.
69. 35. Tian, Z.; Hrinyo-Pavlina, T.; Roeske, R. W.; Rao, P. N.; J. Chromatogr. 1991, 541, 297-302.
70. 36. Fujii, K.; Ikai, Y.; Mayumi, T.; Oka, H.; Suzuki, M.; Harada, K. -i. Anal. Chem. 1997, 69, 3346-3352.
71. 37. We and others have measured enantioselectivities of the optically active Schiff base alkylation products 2b with a variety of chiral HPLC methods. See: (a) Reference 9. (b) Reference 13a. (c) Reference 18a. (d) Reference 31. (e) Lee, W. Anal. Lett. 1997, 30, 2791-2799. (f) Lee, W. Bull. Korean Chem. Soc. 1998, 19, 715-717.
72. 37. We and others have measured enantioselectivities of the optically active Schiff base alkylation products 2b with a variety of chiral HPLC methods. See: (a) Reference 9. (b) Reference 13a. (c) Reference 18a. (d) Reference 31. (e) Lee, W. Anal. Lett. 1997, 30, 2791-2799. (f) Lee, W. Bull. Korean Chem. Soc. 1998, 19, 715-717.
73. 37. We and others have measured enantioselectivities of the optically active Schiff base alkylation products 2b with a variety of chiral HPLC methods. See: (a) Reference 9. (b) Reference 13a. (c) Reference 18a. (d) Reference 31. (e) Lee, W. Anal. Lett. 1997, 30, 2791-2799. (f) Lee, W. Bull. Korean Chem. Soc. 1998, 19, 715-717.
74. 37. We and others have measured enantioselectivities of the optically active Schiff base alkylation products 2b with a variety of chiral HPLC methods. See: (a) Reference 9. (b) Reference 13a. (c) Reference 18a. (d) Reference 31. (e) Lee, W. Anal. Lett. 1997, 30, 2791-2799. (f) Lee, W. Bull. Korean Chem. Soc. 1998, 19, 715-717.
75. 37. We and others have measured enantioselectivities of the optically active Schiff base alkylation products 2b with a variety of chiral HPLC methods. See: (a) Reference 9. (b) Reference 13a. (c) Reference 18a. (d) Reference 31. (e) Lee, W. Anal. Lett. 1997, 30, 2791-2799. (f) Lee, W. Bull. Korean Chem. Soc. 1998, 19, 715-717.
76. 37. We and others have measured enantioselectivities of the optically active Schiff base alkylation products 2b with a variety of chiral HPLC methods. See: (a) Reference 9. (b) Reference 13a. (c) Reference 18a. (d) Reference 31. (e) Lee, W. Anal. Lett. 1997, 30, 2791-2799. (f) Lee, W. Bull. Korean Chem. Soc. 1998, 19, 715-717.
77. 38. The price of 0.1 mole of the parent alkaloids, cinchonidine and cinchonine (see Scheme 3 for structures), is $15.60 and $16.00, respectively (Aldrich Chemical Company Catalog Handbook of Fine Chemicals, 1998-1999).