Diastereoselective aldol reactions of (Z)-N-[bis(methylthio)methylene]- α,β-didehydroglutamates

Journal of Organic Chemistry

Volumn 63, Issue 24, 1998, Pages 8736-8740

  Alvarez Ibarra, Carlos ^a   Csákÿ, Aurelio G ^a   Murcia, M Carmen ^a  

^a UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE DERIVATIVE; ALPHA,BETA DIDEHYDROGLUTAMATE DERIVATIVE; GLUTAMIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DIASTEREOISOMER; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 0031792866     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo980634c     Document Type: Article

References (53)

1. (a) Jung, G. Angew. Chem., Int. Ed. 1991, 30, 1051.
2. (b) Freud, S.; Jung, G.; Gutbrod, O.; Folkers, G.; Gibbons, W. A.; Allgaier, H.; Werner, R. Biopolymers 1991, 31, 803.
3. (c) Noda, K.; Shimohigashi, Y.; Izumya, N. In The Peptides; Academic Press: New York, 1983; Vol. 5, p 285.
4. (d) Schmidt, U.; Liberknecht, A.; Wild, J. Synthesis 1988, 159.
5. (e) Martell, A. E. Acc. Chem. Res. 1989, 22, 115.
6. (d) Cativiela, C.; García, J. I.; Mayoral, J. A.; Pires, E.; Royo, A. J.; Figueras, F. Tetrahedron 1995, 51, 1295.
7. (f) Masquelin, T.; Broger, E.; Müller, K.; Schmid, R.; Obrecht, D. Helv. Chim. Acta 1994, 77, 1395.
8. (g) Shin, C.; Okumura, K.; Ito, A.; Nakamura, Y. Chem. Lett. 1994, 1305.
9. (h) Shimohigashi, Y.; English, M. L.; Stammer, C. H.; Costa, T. Biochem. Biophys. Res. Commun. 1992, 104, 583.
10. (i) Jain, R.; Chauhan, V. S. Biopolymers 1996, 40, 105.
11. (a) Tarzia, G.; Balsamini, C.; Spadoni, G.; Duranti, E. Synthesis 1988, 514.
12. (b) Balsamini, C.; Duranti, E.; Mariani, L.; Salvatori, A.; Spadoni, G. Synthesis 1990, 779.
13. (c) Balsami, C.; Bedini, A.; Galarini, R.; Spadoni, G.; Tarzia, G.; Hamdan, M. Tetrahedron 1994, 50, 12375.
14. (d) Buñuel, E.; Cativiela, C.; Díaz de Villegas, M. D.; Jiménez, A. I. Synlett 1992, 579.
15. (e) Cativiela, C.; Díaz de Villegas, M. D. Tetrahedron 1993, 49, 497.
16. (f) Cativiela, C.; Diaz de Villegas, M. D.; Jiménez, A. I. Tetrahedron 1994, 50, 9157.
17. (g) Cardellicchio, C.; Fiandanese, V.; Marchese, G.; Naso, F.; Ronzini, L. Tetrahedron Lett. 1985, 26, 4387.
18. (h) Buñuel, E.; Cativiela, C.; Díez de Villegas, M. D.; Jiménez, A. I. Synlett 1992, 579.
19. (i) Cativiela, C.; Díez de Villegas, M. D.; Galvez, J. A. Tetrahedron: Asymmetry 1992, 3, 567.
20. (j) Reetz, M. T.; Kayser, F.; Harns, K. Tetrahedron Lett. 1992, 32, 3453.
21. (k) Burk, M. J.; Allen, J. G.; Kiesman, W. F.; Stoffan, K. M. Tetrahedron Lett. 1997, 38, 1309 and references cited therein.
22. (a) Bridges, R. J.; Geddes, J. W.; Monaghan, D. T.; Cotman, C. W. In Excitatory Amino acids in Health and Disease; Lodge, D., Ed.; Wiley: New York, 1988; p 321.
23. (b) Patel, S.; Chapman, A. G.; Millan, M. H.; Meldrum, B. S. In Excitatory Amino Acids in Health and Disease; Lodge, D., Ed.; Wiley: New York, 1988; p 353.
24. (c) Steinberg, G. K.; Saleh, J.; Kuniss, D.; De la Paz, R.; Zarnegar, S. R. Stroke 1989, 20, 1227.
25. (d) Nagamitsu, T.; Sunazuka, T.; Tanaka, H.; Omura, S.; Sprengeler, P. A.; Smith, A. B., III. J. Am. Chem. Soc. 1996, 118, 3584.
26. Alvarez-Ibarra, C.; Csáky, A. G.; Martín, E.; de la Morena, M. J.; Quiroga, M. L. Tetrahedron Lett. 1997, 38, 4501.
27. Arnett, M. E.; Fischer, F. T.; Nichols, M. A.; Ribeiro, A. A. J. Am. Chem. Soc. 1989, 111, 748.
28. (a) Schriltz, D. M.; Kaiseer, R. M.; Hauser, C. H. J. Org. Chem. 1967, 32, 2610.
29. (b) Lee, Y. K.; Schultz, A. G. J. Org. Chem. 1976, 41, 4044.
30. (c) Heathcock, C. H. Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press Inc.: New York, 1984; Vol. 3, p 111.
31. (d) Heathcock, C. H. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. p 181.
32. (a) Bothner-by, A. A.; Naar-Colin, C.; Günther, H. J. Am. Chem. Soc. 1962, 64, 2247.
33. (b) Krebs, E.-P. Helv. Chim. Acta 1981, 64, 1023.
34. (c) Kende, A.; Toder, B. H. J. Org. Chem. 1982, 47, 167.
35. The stereochemical descriptors E and Z are used in this context as recommended by Evans. See: Evans, D. A. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press, Inc.: New York, 1984; Vol. 3, p 11.
36. (a) Adams, A. D.; Schlessinger, R. H.; Tata, J. R.; Venit, J. J. J. Org. Chem. 1986, 51, 3068.
37. (b) Wilson, S. R.; Myers, R. S. J. Org. Chem. 1975, 40, 3309.
38. The most stable chelation of Li and K enolates is usually given by the formation of five-or six-membered rings. However, enolate stabilization by seven-membered rings has also been reported. See for example: Garst, M. E.; Bonfiglio, J. N.; Grudoski, D. A.; Marks, J. J. Org. Chem. 1980, 45, 2307.
39. (a) Dugger, R. W.; Heathcock, C. H. J. Org. Chem. 1980, 45, 1181.
40. (b) Adams, A. D.; Schlessinger, R. H.; Tata, J. R.; Venit, J. J. J. Org. Chem. 1986, 51, 3068.
41. 1H NMR spectrum (300 MHz) with those previously reported for related compounds. See ref 2e and O'Donnell, M. J.; Arasappan, A.; Hornback. W.; Huffman, J. C. Tetrahedron Lett. 1990, 31, 157.
42. Stiles, M.; Winkler, R. R.; Chang, Y.; Traynor, L. J. Am. Chem, Soc. 1964, 86, 3337.
43. House, H. O.; Crumrine, D. S.; Teranishi, A. Y.; Olmstead, H. D. J. Am. Chem. Soc. 1973, 95, 3310.
44. van der Werf, A. W.; Kellog, R. M.; Bolhuis, F. J. Chem. Soc., Chem. Commun. 1991, 682
45. It is well known that silicon enolates are not nucleophilic enough to undergo uncatalyzed addition to aldehydes. See: Chang, T.-H. In Comprehensive Organic Chemistry; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 3, p 595.
46. The trapping of delocalized ester enolates with silylating agents has been reported to be troublesome. See: (a) Corset, J.; Promet, F.; Lautié, M. F.; Ratovelomana, N.; Seyden-Penne, J.; Strzalko, T.; Roux-Schmitt, M. C. J. Am. Chem. Soc. 1993, 115, 1684. (b) Solladié-Cavallo, A.; Csáky, A. G. J. Org. Chem. 1994, 59, 2585 and references cited therein.
47. The trapping of delocalized ester enolates with silylating agents has been reported to be troublesome. See: (a) Corset, J.; Promet, F.; Lautié, M. F.; Ratovelomana, N.; Seyden-Penne, J.; Strzalko, T.; Roux-Schmitt, M. C. J. Am. Chem. Soc. 1993, 115, 1684. (b) Solladié-Cavallo, A.; Csáky, A. G. J. Org. Chem. 1994, 59, 2585 and references cited therein.
48. (a) Heathcock, C. H.; Buse, C. T.; Kleschick, W. A.; Pirrung, M. C.; Sohn, J. E.; Lampe, J. J. Org. Chem. 1980, 45, 1066.
49. (b) Heng, K. K.; Schmith, R. A. J. Tetrahedron 1979, 35, 425.
50. (a) Nakamura, E.; Shimizu, M.; Kuwajima, I. Tetrahedron Lett. 1976, 17, 1699.
51. (b) Nakamura, E.; Yamago, S.; Machii, D.; Kuwajima, I. Tetrahedron Lett. 1988, 29, 2207.
52. (c) Kuwajima, I.; Nakamura, E. Acc. Chem. Res. 1985, 18, 181.
53. Full retroaldolization was observed in an independent essay upon treatment of 8a with 1 M TBAF solution in THF at room temperature in 1 h.