Direct Formation of N-Acylated Amino Acid Derivatives via Nucleophilic Addition to N-Acylimino Esters Using a Polymer-Supported Amine and Scandium Triflate

Journal of Combinatorial Chemistry

Volumn 3, Issue 5, 2001, Pages 401-403

  Kobayashi, Shu ^a   Kitagawa, Hidetoshi ^a   Matsubara, Ryosuke ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; AMINO ACID; MESYLIC ACID DERIVATIVE; POLYMER; SCANDIUM; SCANDIUM TRIFLATE;

ACYLATION; ARTICLE; CHEMISTRY; SYNTHESIS;

ACYLATION; AMINES; AMINO ACIDS; MESYLATES; POLYMERS; SCANDIUM;

EID: 17644438939     PISSN: 15204766     EISSN: None     Source Type: Journal    
DOI: 10.1021/cc010009c     Document Type: Article

References (26)

1. (a) Helms, G. L.; Moore, R. E.; Niemczura, W. P.; Patterson, G. M. L.; Tomer, K. B.; Gross, M. L. J. Org. Chem. 1988, 53, 1298-1307.
2. (b) Matsunaga, S.; Fusetani, N.; Hashimoto, K.; Wälchli, M. J. Am. Chem. Soc. 1989, 111, 2582-2588.
3. (c) Humphrey, J. M.; Chamberlin, A. R. Chem. Rev. 1997, 97, 2243-2266.
4. (d) von Döhren, H.; Keller, U.; Vater, J.; Zocher, R. Chem. Rev. 1997, 97, 2675-2705.
5. For reviews see the following. (a) Dickson, R. C. Annu. Rev. Biochem. 1998, 67, 27-48. (b) Kolter, T.; Sandhoff, K Angew. Chem., Int. Ed. 1999, 38, 1532-1568.
6. For reviews see the following. (a) Dickson, R. C. Annu. Rev. Biochem. 1998, 67, 27-48. (b) Kolter, T.; Sandhoff, K Angew. Chem., Int. Ed. 1999, 38, 1532-1568.
7. (a) Fujii, A.; Hagiwara, E.; Sodeoka, M. J. Am. Chem. Soc. 1999, 121, 5450-5458.
8. (b) Ferraris, D.; Dudding, T.; Young, B.; Drury, W. J., III; Lectka, T. J. Org. Chem. 1999, 64, 2168-2169.
9. (c) Yamada, K.; Harwood, S. J.; Gröger, H.; Shibasaki, M. Angew. Chem., Int. Ed. 1999, 38, 3504-3506.
10. (a) Kober, R.; Papadopoulos, K.; Miltz, W.; Enders, D.; Steglich, W. Reuter, H.; Puff, H. Tetrahedron 1985, 41, 1693-1701.
11. (b) Münster, P.; Steglich, W. Synthesis 1987, 223-225.
12. (c) Bretschneider, T.; Miltz, W.; Münster, P.; Steglich, W. Tetrahedron 1988, 44, 5403-5414.
13. (d) Saaby, S.; Fang, X.; Gathergood, N.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2000, 39, 4114-4116. For a review of N-acyliminium ions and related intermediates, see the following.
14. (e) Speckamp, W. N.; Moolenaar, M. J. Tetrahedron 2000, 56, 3817-3856.
15. For the preparation of N-acyl-α-bromoglycine ethyl esters, see the following. Kober, R.; Steglich, W. Liebigs Ann. Chem. 1983, 599-609.
16. For other methods for the preparations of N-acylimino esters, see the following. (a) Jung, M. E.; Shishido, K.; Light, L.; Davis, L. Tetrahedron Lett. 1981, 22, 4607-4610. (b) Jäger, M.; Polborn, K.; Steglich, W. Tetrahedron Lett. 1995, 36, 861-864.
17. For other methods for the preparations of N-acylimino esters, see the following. (a) Jung, M. E.; Shishido, K.; Light, L.; Davis, L. Tetrahedron Lett. 1981, 22, 4607-4610. (b) Jäger, M.; Polborn, K.; Steglich, W. Tetrahedron Lett. 1995, 36, 861-864.
18. (a) Kobayashi, S. Eur. J. Org. Chem., 1999, 15-27.
19. (b) Kobayashi, S. Synlett 1994, 689-701.
20. For a review see the following. Ley, S. V.; Baxendale, I. R.; Bream, R. N.; Jackson, P. S.; Leach, A. G.; Longbottom, D. A.; Nesi, M.; Scott, J. S.; Storer, R. I.; Taylor, S. J. J. Chem. Soc., Perkin Trans. 1 2000, 3815-4195.
21. (a) Nagayama, S.; Kobayashi, S. Angew. Chem., Int. Ed. 2000, 39, 567-569. See also the following.
22. (b) Kobayashi, S.; Nagayama, S. J. Org. Chem. 1996, 61, 2256-2257.
23. (c) Kobayashi, S.; Nagayama, S. J. Am. Chem. Soc. 1996, 118, 8977-8978.
24. (d) Kobayashi, S.; Nagayama, S.; Busujima, T. Tetrahedron Lett. 1996, 37, 9221-9224.
25. (e) Kobayashi, S.; Nagayama, S. J. Am. Chem. Soc. 1998, 120, 2985-2986.
26. 2O-EtOH (1/1, 20 mL) was added an aqueous NaOH solution (0.1001 N, 3.0 mL). After the mixture was stirred for 3 h, a 0.04% solution of phenolphthalein in EtOH (0.10 mL) was added to the suspension as an indicator. The solution was titrated with an aqueous HCl solution (0.0999 N, 2.60 mL) with stirring. The loading level of 6 was determined to be 0.93 mmol/g.