Direct asymmetric aldol reactions of glycine Schiff base with aldehydes catalyzed by chiral quaternary ammonium salts

Angewandte Chemie - International Edition

Volumn 41, Issue 23, 2002, Pages 4542-4544

  Ooi, Takashi ^a   Taniguchi, Mika ^a   Kameda, Minoru ^a   Maruoka, Keiji ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

Aldol reactions; Amino acids; Asymmetric synthesis; Phase transfer catalysis; Schiff bases

Indexed keywords

ALDEHYDES; AMINO ACIDS; AMMONIUM COMPOUNDS; CATALYSIS; SYNTHESIS (CHEMICAL); TOLUENE;

STEREOCHEMICAL CONTROLS;

STEREOCHEMISTRY;

ALDEHYDE; AMINO ACID DERIVATIVE; AMINOALCOHOL; AMMONIUM BROMIDE; AMMONIUM DERIVATIVE; BETA HYDROXY ALPHA AMINO ACID; GLYCINE; QUATERNARY AMMONIUM DERIVATIVE; SCHIFF BASE; SODIUM HYDROXIDE; TOLUENE; UNCLASSIFIED DRUG;

ALDOL REACTION; AMINO ACID SYNTHESIS; AQUEOUS SOLUTION; ARTICLE; CATALYSIS; CHEMICAL PROCEDURES; CHEMISTRY; CHIRALITY; ENVIRONMENT; STEREOCHEMISTRY; STEREOISOMERISM; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

ALDEHYDES; AMINO ALCOHOLS; CATALYSIS; GLYCINE; QUATERNARY AMMONIUM COMPOUNDS; SCHIFF BASES; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0037011290     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3773(20021202)41:23<4542::AID-ANIE4542>3.0.CO;2-3     Document Type: Article

References (47)

1. a) Glycopeptide Antibiotics (Ed.: R. Nagarajan), Marcel-Dekker, New York, 1994;
2. b) Amino Acids, Peptides and Proteins; Special Periodical Reports; Vols. 1-28, Chemistry Society, London, 19681995;
3. c) M. A. Blaskovich, G. Evindar, N. G. W. Rose, S. Wilkinson, Y. Luo, G. A. Lajoie, J. Org. Chem. 1998, 63, 3631, and references therein.
4. a) G. M. Coppola, H. F. Schuster, Asymmetric Synthesis: Construction of Chiral Molecules Using Amino Acids. Wiley, Toronto, 1987;
5. b) A. Goleciowski, J. Jurczak, Synlett 1993, 241;
6. c) J.-P. Genet, Pure Appl. Chem. 1996, 68, 593.
7. M. J. Miller, Acc. Chem. Res. 1986, 79, 49.
8. a) S. V. Pansare, J. C. Vederas, J. Org. Chem. 1987, 52, 4804;
9. b) R. Badorrey, C. Cativiela, M. D. Diaz-de-Villegas, J. A. Galvez, Tetrahedron: Asymmetry 2000, 11, 1015.
10. D. Tanner, Angew. Chem. 1994, 106, 625; Angew. Chem. Int. Ed. Engl. 1994, 33, 599.
11. D. Tanner, Angew. Chem. 1994, 106, 625; Angew. Chem. Int. Ed. Engl. 1994, 33, 599.
12. a) A. M. P. Koskinen, H. Hasilla, V. T. Myllymaki, K. Rissanen, Tetrahedron Lett. 1995, 36, 5619;
13. b) H. Shao, M. Goodman, J. Org. Chem. 1996, 61, 2582;
14. c) T. Nagamitsu, T. Sunazuka, H. Tanaka, S. Omura, P. A. Sprengeler, A. B. Smith III., J. Am. Chem. Soc. 1996, 118, 3584;
15. d) C. Cativiela, M. D. Diaz-deVillegas, J. A. Galvez, J. I. Garcia, Tetrahedron 1996, 52, 9563;
16. e) M. Horikawa, Y. Shigeri, N. Yumoto, S. Yoshikawa, T. Nakajima, Y. Ohfune, Bioorg. Med. Chem. Lett. 1998, 8, 2027;
17. f) C. A. Hutton, Org. Lett. 1999, 1, 295;
18. g) P. D. Felice, G. Porzi, S. Sandri, Terrahedron: Asymmetry 1999, 10, 2191.
19. With enolates of glycine derivatives: a) S. Kanemasa, T. Mori, A. Tatsukawa, Tetrahedron Lett. 1993, 34, 8293; b) Y. N. Belokon, K. A. Kochetkov, N. S. lkonnikov, T. V. Strelkova, S. R. Harutyunyan, A. S. Saghiyan. Tetrahedron: Asymmetry 2001, 12, 481; c) J. B. MacMillan, T. F. Molinski. Org. Lett. 2002, 4, 1883.
20. With enolates of glycine derivatives: a) S. Kanemasa, T. Mori, A. Tatsukawa, Tetrahedron Lett. 1993, 34, 8293; b) Y. N. Belokon, K. A. Kochetkov, N. S. lkonnikov, T. V. Strelkova, S. R. Harutyunyan, A. S. Saghiyan. Tetrahedron: Asymmetry 2001, 12, 481; c) J. B. MacMillan, T. F. Molinski. Org. Lett. 2002, 4, 1883.
21. With enolates of glycine derivatives: a) S. Kanemasa, T. Mori, A. Tatsukawa, Tetrahedron Lett. 1993, 34, 8293; b) Y. N. Belokon, K. A. Kochetkov, N. S. lkonnikov, T. V. Strelkova, S. R. Harutyunyan, A. S. Saghiyan. Tetrahedron: Asymmetry 2001, 12, 481; c) J. B. MacMillan, T. F. Molinski. Org. Lett. 2002, 4, 1883.
22. For a few examples in which a catalytic amount of chiral sources is employed, see: a) Y. Ito, M. Sawamura, E. Shirakawa, K. Hayashizaki, T. Hayashi, Tetrahedron 1988, 44, 5253; b) H. Suga, K. Ikai, T. Ibata, Tetrahedron Lett. 1998, 39, 869; c) D. A. Evans, J. M. Janey, N. Magomedov, J. S. Tedrow, Angew. Chem. 2001, 113, 1936; Angew. Chem. Int. Ed. 2001, 40, 1884.
23. For a few examples in which a catalytic amount of chiral sources is employed, see: a) Y. Ito, M. Sawamura, E. Shirakawa, K. Hayashizaki, T. Hayashi, Tetrahedron 1988, 44, 5253; b) H. Suga, K. Ikai, T. Ibata, Tetrahedron Lett. 1998, 39, 869; c) D. A. Evans, J. M. Janey, N. Magomedov, J. S. Tedrow, Angew. Chem. 2001, 113, 1936; Angew. Chem. Int. Ed. 2001, 40, 1884.
24. For a few examples in which a catalytic amount of chiral sources is employed, see: a) Y. Ito, M. Sawamura, E. Shirakawa, K. Hayashizaki, T. Hayashi, Tetrahedron 1988, 44, 5253; b) H. Suga, K. Ikai, T. Ibata, Tetrahedron Lett. 1998, 39, 869; c) D. A. Evans, J. M. Janey, N. Magomedov, J. S. Tedrow, Angew. Chem. 2001, 113, 1936; Angew. Chem. Int. Ed. 2001, 40, 1884.
25. For a few examples in which a catalytic amount of chiral sources is employed, see: a) Y. Ito, M. Sawamura, E. Shirakawa, K. Hayashizaki, T. Hayashi, Tetrahedron 1988, 44, 5253; b) H. Suga, K. Ikai, T. Ibata, Tetrahedron Lett. 1998, 39, 869; c) D. A. Evans, J. M. Janey, N. Magomedov, J. S. Tedrow, Angew. Chem. 2001, 113, 1936; Angew. Chem. Int. Ed. 2001, 40, 1884.
26. For a recent review on the direct catalytic asymmetric aldol reaction, see: a) B. Alcaide, P. Almendros, Eur. J. Org. Chem. 2002, 1595; see also: b) R. Mahrwald, Chem. Rev. 1999, 1095; c) T. D. Machajewski, C.-H. Wong, Angew. Chem. 2000, 112, 1406; Angew. Chem. Int. Ed. 2000, 39, 1352.
27. For a recent review on the direct catalytic asymmetric aldol reaction, see: a) B. Alcaide, P. Almendros, Eur. J. Org. Chem. 2002, 1595; see also: b) R. Mahrwald, Chem. Rev. 1999, 1095; c) T. D. Machajewski, C.-H. Wong, Angew. Chem. 2000, 112, 1406; Angew. Chem. Int. Ed. 2000, 39, 1352.
28. For a recent review on the direct catalytic asymmetric aldol reaction, see: a) B. Alcaide, P. Almendros, Eur. J. Org. Chem. 2002, 1595; see also: b) R. Mahrwald, Chem. Rev. 1999, 1095; c) T. D. Machajewski, C.-H. Wong, Angew. Chem. 2000, 112, 1406; Angew. Chem. Int. Ed. 2000, 39, 1352.
29. For a recent review on the direct catalytic asymmetric aldol reaction, see: a) B. Alcaide, P. Almendros, Eur. J. Org. Chem. 2002, 1595; see also: b) R. Mahrwald, Chem. Rev. 1999, 1095; c) T. D. Machajewski, C.-H. Wong, Angew. Chem. 2000, 112, 1406; Angew. Chem. Int. Ed. 2000, 39, 1352.
30. For a synthesis that leads to products with low ee values see: C. M. Gasparski, M. J. Miller, Tetrahedron 1991, 47, 5367.
31. For a Mukaiyama-type reaction with ketene silyl acetal of glycine Schiff base. see: M. Horikawa, J. Busch-Petersen, E. J. Corey, Tetrahedron Lett. 1999, 40, 3843.
32. a) A. Saeed, D. W. Young, Tetrahedron 1992, 48, 2507;
33. b) V. P. Vassilev, T. Uchiyama, T. Kajimoto, C.-H. Wong, Tetrahedron Lett. 1995, 36, 5063;
34. c) T. Kimura, V. P. Vassilev, G.-J., Shen, C.-H. Wong, J. Am. Chem. Soc. 1997, 119, 11 734;
35. d) T. Miura, M. Fujii, K. Shingu, I. Koshimizu, J. Naganoma, T. Kajimoto, Y. Ida, Tetrahedron Lett. 1998, 39, 7313;
36. e) N. Wymer, E. J. Toone, Curr. Opin. Chem. Biol. 2000, 4, 110;
37. f) B. G. Jackson, S. W. Pedersen, J. W. Fisher, J. W. Misner, J. P. Gardner, M. A. Staszak, C. Doecke, J. Rizzo, J. Aikins, E. Farkas, K. L. Trinkle, J. Vicenzi, M. Reinhard, E. P. Kroeff, C. A. Higginbotham, R. J. Gazak, T. Y. Zhang, Tetrahedron 2000, 56, 5667.
38. For reviews on the use of glycine Schiff base for the preparation of enantiomerically pure α-amino acids, see: a) T. Abellan, R. Chinchilla, N. Galindo, G. Guillena, C. Najera, J. M. Sansano, Eur. J. Org. Chem. 2000, 2689; b) M. J. O'Donnell, Aldrichimica Acta 2001, 34, 3.
39. For reviews on the use of glycine Schiff base for the preparation of enantiomerically pure α-amino acids, see: a) T. Abellan, R. Chinchilla, N. Galindo, G. Guillena, C. Najera, J. M. Sansano, Eur. J. Org. Chem. 2000, 2689; b) M. J. O'Donnell, Aldrichimica Acta 2001, 34, 3.
40. a) T. Ooi, M. Kameda, K. Maruoka, J. Am. Chem. Soc. 1999, 121, 6519;
41. b) T. Ooi, M. Takeuchi, M. Kameda, K. Maruoka, J. Am. Chem. Soc. 2000, 122, 5228;
42. c) T. Ooi, M. Kameda, H. Tannai, K. Maruoka, Tetrahedron Lett. 2000, 41, 8339;
43. d) T. Ooi, K. Doda, K. Maruoka, Org. Lett. 2001, 3, 1273;
44. e) T. Ooi, M. Takeuchi, K. Maruoka, Synthesis 2001, 1716.
45. 2) in 60% yield with an anti/syn ratio of 1:5.3: the enantiomeric excess of the major syn isomer was 25%. Similar syn selectivity was observed in the Mukaiyama-type reaction catalyzed by the cinchonidine-derived bifluoride salt.[11]
46. M. M. Palian, R. Polt, J. Org. Chem. 2001, 66, 7178.
47. 3) with HCl (6N) in MeOH gave rise to the corresponding β-hydroxy-α-amino acid hydrochloride: its absolute configuration was determined to be 2S,3S by comparison of the optical rotation value with that of the hydrochloride salt of commercially available L-allo-threonine.