Highly enantioselective epoxidation of 2-methylnaphthoquinone (vitamin K3) mediated by new cinchona alkaloid phase-transfer catalysts

Chemistry - A European Journal

Volumn 13, Issue 16, 2007, Pages 4483-4498

  Berkessel, Albrecht ^a   Guixà, Maria ^a   Schmidt, Friederike ^a   Neudörfl, Jörg M ^a   Lex, Johann ^a  

^a UNIVERSITY OF COLOGNE   (Germany)

Author keywords

Alkaloids; Asymmetric catalysis; Enones; Epoxidation; Phase transfer catalysis

Indexed keywords

ALKYLATION; ANTHRACENE; CHIRALITY; EPOXIDATION; KETONES; OXIDANTS;

ALKALOIDS; COMPUTATIONAL ANALYSIS; ENONES; PHASE TRANSFER CATALYSTS;

VITAMINS;

CINCHONA ALKALOID; EPOXIDE; MENADIONE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; COMPUTER SIMULATION; CONFORMATION; OXIDATION REDUCTION REACTION; PHASE TRANSITION; STEREOISOMERISM; SYNTHESIS;

CATALYSIS; CINCHONA ALKALOIDS; COMPUTER SIMULATION; EPOXY COMPOUNDS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; PHASE TRANSITION; STEREOISOMERISM; VITAMIN K 3;

EID: 34250344104     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200600993     Document Type: Article

References (46)

1. C. Bonini, G. Righi, Tetrahedron 2002, 58, 4981-5021.
2. T. Katsuki, in Comprehensive Asymmetric Catalysis (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Berlin, 1999, pp. 621-648.
3. E. N. Jacobsen, M. H. Wu, in Comprehensive Asymmetric Catalysis (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Berlin, 1999, pp. 649-677.
4. A. Berkessel, H. Gröger. in Asymmetric Organocatalysia, Wiley-VCH, Weinheim, 2005, pp. 290-303.
5. M. J. Porter, J. Skidmore, J. Chem. Soc. Chem. Commun. 2000, 1215-1225.
6. Y. Shi, Acc. Chem. Res. 2004, 37, 488-496.
7. S. Matsunaga, T. Kinoshita, S. Okada, S. Harada, M. Shibasaki, J. Am. Chem. Soc. 2004, 126, 7559-7570.
8. M. Marigo, J. Franzén, T. B. Poulsen, W. Zhuang, K. A. Jørgensen, J. Am. Chem. Soc. 2005, 127, 6964-6965.
9. T. Ooi, D. Ohara, M. Tamura, K. Maruoka, J. Am. Chem. Soc. 2004, 126, 6844-6845.
10. R. Helder, J. C. Hummelen, R. W. P. M. Laane, J. S. Wiering, H. Wynherg. Tetrahedron Lett. 1976, 17, 1831-1834.
11. J. C. Hummclen, H. Wynberg, Tetrahedron Lett. 1978, 19, 1089-1092.
12. H. Wynberg, B. Greijdanus, J. Chem. Soc. Chem. Commun. 1978, 427-428.
13. E. J. Corey, F.-Y. Zhang, Org. Lett. 1999, 1, 1287-1290.
14. B. Lygo, P. G. Wainwright, Tetrahedron Lett. 1998, 39, 1599-1602.
15. B. Lygo, D. C. M. To, Tetrahedron Lett. 2001, 42, 1343-1346.
16. S. Arai, H. Tsuge, M. Oku, M. Miura, T. Shioiri, Tetrahedron 2002, 58, 1623-1630.
17. L. Alcaraz, G. Macdonald, J. P. Ragot, N. Lewis, R. J. K. Taylor, J. Org. Chem. 1998, 63, 3526-3527.
18. A. Bundu, N. G. Berry, C. D. Gill, CL. Dwyer, A. V. Stachulski, R. J. K. Taylor, J. Whittall, Tetrahedron: Asymmetry 2005, 16, 283-293.
19. C. L. Dwyer, C. D. Gill, O. Ichihara, R. J. K. Taylor, Synlett 2000, 704-706.
20. S. Arai, M. Oku, M. Miura, T. Shioiri, Synlett 1998, 1201-1202.
21. T. Perrard, J.-C. Plaquevent, J.-R. Desmurs, D. Hébrault, Org. Lett. 2000, 2, 2959-2962.
22. H. Li, Y. Wang, L. Tang, L. Deng, J. Am. Chem. Soc. 2004, 126, 9906-9907.
23. X. Liu, H. Li, L. Deng, Org. Lett. 2005, 7, 167-169.
24. Y. Iwabuchi, M. Nakatani, N. Yokoyama, S. Hatakeyama, J. Am. Chem. Soc. 1999, 121, 10 219-10 220.
25. W. M. Braje, J. Holzgrefe, R. Wartchow, H. M. R. Hoffmann, Angew. Chem. 2000, 112, 2165-2167;
26. Angew. Chem. Int. Ed. 2000, 39, 2085-2087.
27. R. L. Halterman, S.-T. Jan, J. Org. Chem. 1991, 56, 5253-5254.
28. R. L. Halterman, S.-T. Jan, A. H. Abdulwali, D. J. Standlee, Tetrahedron 1997, 53, 11 277-11 296.
29. R. L. Halterman, S.-T. Jan, H. L. Nimmons, D. J. Standlee, M. A. Khan, Tetrahedron 1997, 53, 11 257-11 276.
30. H. Sasaki, R. Irie, T. Katsuki, Synlett 1993, 300-302.
31. Y. Uozumi, N. Suzuki, A. Ogiwara, T. Hayashi, Tetrahedron 1994, 50, 4293-4302.
32. T. Hayashi, K. Hayashizaki, T. Kiyoi, Y. Ito, J. Am. Chem. Soc. 1988, 110, 8153-8156.
33. E. J. Corey, F. Xu, M. C. Noe, J. Am. Chem. Soc. 1997, 119, 12 414-12 415.
34. E. J. Corey, Y. Bo, J. Busch-Petersen J. Am. Chem. Soc. 1998, 120, 13 000-13 001.
35. E. J. Corey, M. C. Noe, A. Y. Ting, Tetrahedron Lett. 1996, 37, 1735-1738.
36. H. Pluim, H. Wynberg, J. Org. Chem. 1980, 45, 2498-2502.
37. D. S. R. Rao, Indian J. Chem. Sect. B 1981, 20B, 786-789.
38. S. P. Mathew, S. Gunathilagan, S. M. Roberts, D. G. Blackmond, Org. Lett. 2005, 7, 4847-4850.
39. C. A. Bunton, G. J. Minkoff, J. Chem. Soc. 1949, 665-670.
40. G. Snatzke, H. Wynberg, B. Feringa, B. G. Marsman, B. Greydanus, H. Pluim, J. Org. Chem. 1980, 45, 4094-4096.
41. M. E. Grimaux, R. Arnaud, Bull. Soc. Chim. Fr. 1892, 7, 304-312.
42. J. C. Ghosh, I. B. Chatterjce, J. Ind. Chem. 1931, 8, 257-258.
43. Y. Yanuka, S. Yosselson-Superstine, A. Geryes, E. Superstine, J. Pharm. Sci. 1981, 70, 675-679.
44. T. A. Henry, W. Solomon, J. Chem. Soc. 1934, 1923-1929.
45. G. Giemsa, K. Bonath, Chem. Ber. 1925, 58, 87-96.
46. S. Miyano, S. Okada, T. Suzuki, S. Hancia, H. Hashimoto, Bull. Chem. Soc. Jpn. 1986, 59, 2044-2046.