Enantioselective synthesis of β-hydroxy-α-amino acid esters by aldol coupling using a chiral quaternary ammonium salt as catalyst

Tetrahedron Letters

Volumn 40, Issue 20, 1999, Pages 3843-3846

  Horikawa, Manabu ^a   Busch Petersen, Jakob ^a   Corey, E J ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; CINCHONIDINE; ESTER DERIVATIVE; FLUORIDE; HYDROXYAMINO ACID; IMIDAZOLE DERIVATIVE; QUATERNARY AMMONIUM DERIVATIVE; THIOCARBAMIC ACID DERIVATIVE;

ARTICLE; CATALYST; CHEMICAL REACTION; CHIRALITY; ENANTIOMER; EXTRACTION; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033553450     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00636-X     Document Type: Article

References (25)

1. 1. Corey, E. J.; Xu, F.; Noe, M. C. J. Am. Chem. Soc. 1997, 119, 12414.
2. 2. Corey, E. J.; Bo, Y.; Busch-Petersen, J. J. Am. Chem. Soc. 1998, 120, 13000.
3. 3. Corey, E. J.; Noe, M. C.; Xu, F. Tetrahedron Letters 1998, 39, 5347.
4. 4. For references to earlier work on enantioselective phase transfer catalyzed alkylation, see (a) Dolling, U.-H.; Davis, P.; Grabowski, E. J. J. J. Am. Chem. Soc. 1984, 106, 446.
5. (b) Hughes, D. L.; Dolling, U.-H.; Ryan, K. M; Schoenewaldt, E. F.; Grabowski, E. J. J. J. Org. Chem. 1987, 52, 4745.
6. (c) O'Donnell, M. J.; Bennett, W. D.; Wu, S. J. Am. Chem. Soc. 1989, 111, 2353.
7. (d) O'Donnell, M. J.; Wu, S.; Huffman, J. C. Tetrahedron 1994, 50, 4507.
8. (e) Lipkowitz, K. B.; Cavanaugh, M. W.; Baker, B.; O'Donnell, M. J. J. Org. Chem. 1991, 56, 5181.
9. (f) O'Donnell, M. J.; Esikova, I. A.; Mi, A.; Shullenberger, D. F.; Wu, S. in Phase-Transfer Catalysis, M. E. Halpern, Ed., ACS Symposium Series 659, American Chemical Society, Washington, D.C., 1997, Chapter 10.
10. 5.
11. 2 solution at room temperature and should be kept cold.
12. 7. Corey, E. J.; Lee, D.-H.; Choi, S. Tetrahedron Letters 1992, 33, 6735.
13. 8. For other syntheses of isomeric β-hydroxyleucines, see (a) Schollkopf, U.; Groth, U.; Gull, M.-R.; Nozulak, J. Liebigs Ann.Chem. 1983, 1133.
14. (b) Jung, M. E.; Jung, Y. H. Tetrahedron Letters 1989, 30, 6637.
15. (c) Caldwell, C. G.; Bondy, S. S. Synth. 1990, 34.
16. (d) Blaser, D.; Seebach, D. Liebigs Ann. Chem. 1991, 1067.
17. (e) Sunazuka, T.; Nagamitsu, T.; Tanaka, H.; Omura, S.; Sprengeler, P. A.; Smith, III, A. B. Tetrahedron Letters 1993, 34, 4447.
18. (f) Panek, J. S.; Masse, C. E. J. Org. Chem. 1998, 63, 2382.
19. +, 246.1164; found, 246.1154.
20. 10. Boger, D. L.; Colletti, S. L.; Honda, T.; Menezes, R. F. J. Am. Chem. Soc. 1994, 116, 5607.
21. 11. (a) Battistini, L.; Zanardi, F.; Rassu, G.; Spanu, P.; Pelosi, G.; Fava, G. G.; Ferrari, M. B.; Casiraghi, G. Tetrahedron: Asymmetry 1997, 8, 2975.
22. (b) Greek, C.; Ferreira, F.; Genet, J. P. Tetrahedron Letters 1996, 37, 2031.
23. (c) Agami, C.; Couty, F.; Mathieu, H. Tetrahedron Letters 1996, 37, 4001.
24. 12. See Williams, R. M.; Sinclair, P. J.; Zhai, D.; Chen, D. J. Am. Chem. Soc. 1988, 110, 1547.
25. 13. This research was assisted financially by grants from the National Science Foundation and the National Institutes of Health. M.H. gratefully acknowledges support by the Suntory Institute for Bioorganic Research.