Oxazaborolidine catalysed enantioselective reduction of cyclic meso-imides

Tetrahedron Asymmetry

Volumn 8, Issue 11, 1997, Pages 1773-1789

  Ostendorf, Martin ^a   Romagnoli, Romeo ^a   Pereiro, Isabel Cabeza ^a   Roos, Eric C ^a   Moolenaar, Marinus J ^a   Speckamp, W Nico ^a   Hiemstra, Henk ^a  

^a UNIVERSITY OF AMSTERDAM   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

IMIDE; LACTAM DERIVATIVE;

ARTICLE; CATALYSIS; DRUG SYNTHESIS; ENANTIOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0030908125     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(97)00154-7     Document Type: Article

References (25)

1. (a) Mukaiyama, T.; Yamashita, H.; Asami, M. Chem. Lett. 1983, 385.
2. (b) Miller, S. A.; Chamberlin, A. R. J. Org. Chem. 1989, 54, 2502.
3. (a) Matsuki, K.; Inoue, H.; Ishida, A.; Takeda, M. Heterocycles 1993, 36, 937.
4. (b) Matsuki, K.; Inoue, H.; Ishida, A.; Takeda, M.; Nakagawa, M.; Hino, T. Chem. Pharm. Bull. 1994, 42, 9.
5. Kang, J.; Lee, J. W.; Kim, J. I.; Pyun, C. Tetrahedron Lett. 1995, 36, 4265.
6. Ramón, D. J.; Guillena, G.; Seebach, D. Helv. Chim. Act. 1996, 79, 875.
7. (a) Hirao, A.; Itsuno, S.; Nakahama, S.; Yamazaki, N. J. J. Chem. Soc., Chem. Commun. 1981, 315.
8. (b) Corey, E. J.; Bakshi, R. K.; Shibata, S. J. Am. Chem. Soc. 1987, 109, 5551.
9. (c) Mathre, E. J.; Jones, T. K.; Xavier, L. C.; Blacklock, T. J.; Reamer, R. A.; Mohan, J. J.; Turner Jones, E. T; Hoogsteen, K.; Baum, M. W.; Grabowski, E. J. J. J. Org. Chem. 1991, 56, 751.
10. (d) Jones, T. K.; Mohan, J. J.; Xavier, L. C.; Blacklock, T. J.; Mathre, E. J.; Sohar, P.; Turner Jones, E. T.; Reamer, R. A.; Roberts, F.; Grabowski, E. J. J. J. Org. Chem. 1991, 56, 763.
11. (e) Xavier, L. C.; Mohan, J. J.; Mathre, D. J.; Thompson, A. S.; Carroll, J. D.; Corly, E. G.; Desmond, R. Org. Synth. 1996, 74, 50.
12. Reviews: (f) Wallbaum, S.; Martens, J. Tetrahedron: Asymm. 1992, 3, 1475.
13. (f) Deloux, L.; Srebnik, M. Chem. Rev. 1993, 93, 763.
14. Hubert, J. C.; Steege, W.; Speckamp, W. N.; Huisman, H. O. Synth. Commun. 1971, 1, 103.
15. Romagnoli, R.; Roos, E. C.; Hiemstra, H.; Moolenaar, M. J.; Speckamp, W. N.; Kaptein, B.; Schoemaker, H. E. Tetrahedron Lett. 1994, 35, 1087.
16. Layton, L.; McCoy, L. J. Am. Chem. Soc. 1958, 80, 6568.
17. (a) Rice, L. M.; Grogan, C. H. J. Org. Chem. 1959, 24, 7.
18. (b) Crockett, G. C.; Koch, T. H. J. Org.Chem. 1977, 42, 2721.
19. Kwart, H.; Burchuk, I. J. Am. Chem. Soc. 1952, 74, 3094.
20. Roberts, J. D.; Lee, C. C.; Saunders, W. H. J. Am. Chem. Soc. 1954, 76, 4501.
21. Jakovac, I. J.; Goodbrand, H. B.; Lok, K. P.; Jones, J. B. J. Am. Chem. Soc. 1982, 104, 4659.
22. Süess, R. Helv. Chim. Act. 1977, 60, 1650.
23. Brown, D. S.; Charreau, P.; Hansson, T.; Ley, S. V. Tetrahedron 1991, 47, 1311.
24. Dijkink, J.; Goubitz, K.; Van Zanden, M. N. A.; Hiemstra, H. Tetrahedron: Asymm. 1996, 7, 515.
25. Rice, L. M.; Grocan, C. H. J. Org. Chem. 1957, 22, 1100.