Ru(II)-catalyzed asymmetric cyclopropanation using chiral diphenylphosphino(oxazolinyl)quinoline ligands

Tetrahedron Asymmetry

Volumn 10, Issue 10, 1999, Pages 1903-1911

  Park, Sang Wook ^a   Son, Jeong Ho ^a   Kim, Sung Gon ^a   Ahn, Kyo Han ^a  

^a Pohang University of Science and Technology (POSTECH)   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

QUINOLINE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; SYNTHESIS; THERMOSTABILITY;

EID: 0033591116     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(99)00190-1     Document Type: Article

References (28)

1. Kim, S. G.; Cho, C. W.; Ahn, K. H. Tetrahedron: Asymmetry 1997, 8, 1023.
2. (a) Lowenthal, R. E.; Abiko, A.; Masamune, S. Tetrahedron Lett. 1990, 31, 6005.
3. (b) Lowenthal, R. E.; Masamune, S. Tetrahedron Lett. 1991, 32, 7373.
4. (c) Evans, D. A.; Woerpel, K. A.; Hinman, M. M.; Faul, M. M. J. Am. Chem. Soc. 1991, 113, 726.
5. (d) Müller, D.; Umbricht, G.; Weber, B.; Pfaltz, A. Helv. Chim. Acta 1991, 74, 232.
6. Nishiyama, H.; Itoh, Y.; Matsumoto, H.; Park, S. B.; Itoh, K. J. Am. Chem. Soc. 1994, 116, 2223.
7. Park, S. B.; Sakata, N.; Nishiyama, H. Chem. Eur. J. 1996, 2, 303.
8. (a) Williams, J. M. J. Synlett 1996, 705.
9. (b) Pfaltz, A. Acta Chem. Scand. 1996, 50, 189.
10. (c) Lightfoot, A.; Schnider, P.; Pfaltz, A. Angew. Chem., Int. Ed. Engl. 1998, 37, 2897.
11. (d) Schnider, P.; Koch, G.; Prétôt, R.; Wang, G.; Bohnen, F. M.; Krüger, C.; Pfaltz, A. Chem. Eur. J. 1997, 3, 887.
12. Krasavin, I. A.; Dziomko, V. M.; Radin, Y. P. Metody Polucheniya Khim, Reactivov i Preparatov. 1965, 13, 68; 1965, 13, 94; Chem. Abstr. 1966, 65, 5437b; 7139a. Clark, C. R.; Hay, R. W J. Chem. Soc., Dalton Trans. 1974, 2148.
13. Krasavin, I. A.; Dziomko, V. M.; Radin, Y. P. Metody Polucheniya Khim, Reactivov i Preparatov. 1965, 13, 68; 1965, 13, 94; Chem. Abstr. 1966, 65, 5437b; 7139a. Clark, C. R.; Hay, R. W J. Chem. Soc., Dalton Trans. 1974, 2148.
14. Krasavin, I. A.; Dziomko, V. M.; Radin, Y. P. Metody Polucheniya Khim, Reactivov i Preparatov. 1965, 13, 68; 1965, 13, 94; Chem. Abstr. 1966, 65, 5437b; 7139a. Clark, C. R.; Hay, R. W J. Chem. Soc., Dalton Trans. 1974, 2148.
15. Krasavin, I. A.; Dziomko, V. M.; Radin, Y. P. Metody Polucheniya Khim, Reactivov i Preparatov. 1965, 13, 68; 1965, 13, 94; Chem. Abstr. 1966, 65, 5437b; 7139a. Clark, C. R.; Hay, R. W J. Chem. Soc., Dalton Trans. 1974, 2148.
16. Bolm, C.; Weickhardt, K.; Zehnder, M.; Ranff, T. Chem. Ber. 1991, 124, 1173.
17. (a) Ager, D. J.; East, M. B.; Eisenstadt, A.; Laneman, S. A. Chem. Commun. 1997, 2359.
18. (b) For a similar observation, see: Bremberg, U.; Rahm, F.; Moberg, C. Tetrahedron: Asymmetry 1998, 9, 3437.
19. Nishiyama, H.; Soeda, N.; Naito, T.; Motoyama, Y. Tetrahedron: Asymmetry 1998, 9, 2865.
20. (a) Doyle, M. P. Recl. Trav. Chim. Pays Bas 1991, 110, 305.
21. (b) Doyle, M. P. Aldrichimica Acta 1996, 29, 3.
22. (c) Gant, T. G.; Noe, M. C.; Corey, E. J. Tetrahedron Lett. 1995, 36, 8745.
23. (d) Doyle, M. P.; Peterson, C. S.; Parker Jr., D. L. Angew. Chem., Int. Ed. Engl. 1996, 35, 1334.
24. (e) Piqué, C.; Fähndrich, B.; Pfaltz, A. Synlett 1995, 491.
25. (f) Doyle, M. P.; Peterson, C. S.; Zhou, Q. L.; Nishiyama, H. Chem. Commun. 1997, 211.
26. The diazo compounds were synthesized according to the literature procedures. 11-13: Mori, K.; Matsui, M. Tetrahedron 1969, 25, 5013. 14: Taber, D. F.; Ruckle Jr., R. E.; Hennessy, M. J. J. Org. Chem. 1986, 51, 4077. 15: Doyle, M. P.; Austin, R. E.; Bailey, A. S.; Dwyer, M. P.; Dyatkin, A. B.; Kalinin, A. V.; Kwan, M. M. Y.; Liras, S.; Oalmann, C. J.; Pieters, R. J.; Protopopova, M. N.; Raab, C. E.; Roos, G. H. P.; Zhou, Q. L.; Martin, S. F. J. Am. Chem. Soc. 1995, 117, 5763.
27. The diazo compounds were synthesized according to the literature procedures. 11-13: Mori, K.; Matsui, M. Tetrahedron 1969, 25, 5013. 14: Taber, D. F.; Ruckle Jr., R. E.; Hennessy, M. J. J. Org. Chem. 1986, 51, 4077. 15: Doyle, M. P.; Austin, R. E.; Bailey, A. S.; Dwyer, M. P.; Dyatkin, A. B.; Kalinin, A. V.; Kwan, M. M. Y.; Liras, S.; Oalmann, C. J.; Pieters, R. J.; Protopopova, M. N.; Raab, C. E.; Roos, G. H. P.; Zhou, Q. L.; Martin, S. F. J. Am. Chem. Soc. 1995, 117, 5763.
28. The diazo compounds were synthesized according to the literature procedures. 11-13: Mori, K.; Matsui, M. Tetrahedron 1969, 25, 5013. 14: Taber, D. F.; Ruckle Jr., R. E.; Hennessy, M. J. J. Org. Chem. 1986, 51, 4077. 15: Doyle, M. P.; Austin, R. E.; Bailey, A. S.; Dwyer, M. P.; Dyatkin, A. B.; Kalinin, A. V.; Kwan, M. M. Y.; Liras, S.; Oalmann, C. J.; Pieters, R. J.; Protopopova, M. N.; Raab, C. E.; Roos, G. H. P.; Zhou, Q. L.; Martin, S. F. J. Am. Chem. Soc. 1995, 117, 5763.