Enantioselective hydrogenation of 2-methylquinoxaline to (-)-(2S)-2-methyl-1,2,3,4-tetrahydroquinoxaline by iridium catalysis

Organometallics

Volumn 17, Issue 15, 1998, Pages 3308-3310

  Bianchini, Claudio ^a   Barbaro, Pierluigi ^a   Scapacci, Giancarlo ^a   Farnetti, Erica ^b   Graziani, Mauro ^b  

^a CNR   (Italy)

^b UNIVERSITY OF TRIESTE   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000218673     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om980219a     Document Type: Article

References (25)

1. (a) Butera, J. A.; Spinelli, W.; Anantharaman, V.; Marcopulos, N.; Parsons, R. W.; Moubarak, I. F.; Cullinan, C.; Bagli, J. F. J. Med. Chem. 1991, 34, 3212.
2. (b) Aguilera, R.; Duplant, J.-C.; Nofre, C. Bull. Soc. Chim. Fr. 1968, 11, 4491.
3. (c) Armarego, W. L. F.; Waring, P.; Paal, B. Aust. J. Chem. 1982, 35, 785.
4. (d) Fisher, G. H.; Schultz, H. P. J. Org. Chem. 1974, 39, 635.
5. (e) Battistini, M.; Erba, E.; Pocar, D. J. Chem. Soc., Perkin Trans. 1993, 339.
6. (f) Matsuura, S.; Sugimoto, T.; Haegawa, H.; Imaizumi, S.; Ichiyama, A. J. Biochem. (Tokyo) 1980, 87, 951.
7. (a) Takaya, H.; Ohta, T.; Noyori, R. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993; p 31.
8. (b) James, B. R. Catal. Today 1997, 37, 209.
9. (a) Uematsu, N.; Fujii, A.; Hashiguchi, S.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1996, 118, 4916.
10. (b) Brunner, H.; Huber, C. Chem. Ber. 1992, 125, 2085.
11. (c) Schnider, P.; Koch, G.; Prétôt, R.; Wang, G.; Bohnen, F. M.; Krüger, C.; Pfaltz, A. Chem. Eur. J. 1997, 3, 887.
12. Murata, S.; Sugimoto, T.; Matsuura, S. Heterocycles 1987, 26, 763.
13. (a) Bianchini, C.; Farnetti, E.; Glendenning, L.; Graziani, M.; Nardin, G.; Peruzzini, M.; Rocchini, E.; Zanobini, F. Organometallics 1995, 14, 1489.
14. (b) Bianchini, C.; Glendenning, L.; Peruzzini, M.; Purches, G.; Zanobini, F.; Farnetti, E.; Graziani, M.; Nardin, G. Organometallics 1997, 16, 4414.
15. (c) Bianchini, C.; Glendenning, L.; Zanobini, F.; Farnetti, E.; Graziani, M.; Nagy, E. J. Mol. Catal. A: Chem. 1998, 132, 13.
16. (a) Bianchini, C.; Meli, A.; Patinec, V.; Sernau, V.; Vizza, F. J. Am. Chem. Soc. 1997, 119, 4945.
17. (b) Bianchini, C.; Meli, A.; Traversi, A. IT, FI97 A000025 1997.
18. (a) Bacalski, A. G.; Cullen, W. R.; Fryzuk, M. D. James, B. R.; Kang, G.-J, Rettig, S. Inorg. Chem. 1991, 30 15002.
19. (b) Spindler, F.; Pugin, B.; Blaser, H.-U. Angew. Chem., Int. Ed. Engl. 1990, 29, 558.
20. (a) Bedford, R. B.; Castillon, S.; Chaloner, PA; Claver, C.; Fernandez, E.; Hitchcock, P. B.; Ruiz, A. Organometallics 1996, 15, 3990.
21. (b) Lewis, L. N. J. Am. Chem. Soc. 1986, 108, 743.
22. Willoughby, C. A.; Buchwald, S. I. J. Am. Chem. Soc. 1994, 116, 8952.
23. (a) Ng Cheong Chan, Y.; Osborn, J. A. J. Chem. Soc., Chem. Commun. 1990, 869.
24. (b) Ng Cheong Chan, Y.; Osborn, J. A. J. Am. Chem. Soc. 1990, 112, 9400.
25. 5b,c At room temperature, a dihydrogen pressure higher than 7 bar is necessary to induce the formation of an equilibrium concentration of (R)-2, while a pressure of 20 bar is required at the catalytic temperature (70-100°C).