Asymmetric Pt(II)-catalyzed ene reactions: Counterion-dependent additive and diphosphine electronic effects

Organic Letters

Volumn 3, Issue 8, 2001, Pages 1233-1236

  Koh, Jeong Hwan ^a   Larsen, Andrew O ^a   Gagné, Michel R ^a  

^a University of North Carolina at Chapel Hill   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANION; ION; LIGAND; PHENOL; PHOSPHINE DERIVATIVE; PLATINUM;

ARTICLE; CHEMICAL MODEL; CHEMISTRY;

ANIONS; IONS; LIGANDS; MODELS, CHEMICAL; PHENOL; PHOSPHINES; PLATINUM;

EID: 0035912368     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol015702n     Document Type: Article

References (43)

1. We dedicate this paper to Prof. David A. Evans of Harvard University, on the occasion of his 60th birthday.
2. For general Cu(II) Lewis acid references, see: (a) Johnson, J. S.; Evans, D. A. Acc. Chem. Res. 2000, 33, 325-335.
3. (b) Jørgensen, K. A.; Johannsen, M.; Yao, S.; Audrain, H.; Thorhauge, J. Acc. Chem. Res. 1999, 32, 605-613.
4. (c) Gothelf, K. V.; Jørgensen, K. A. Chem. Commun. 2000, 1449-1458.
5. (d) Jørgensen, K. A. Angew. Chem., Int. Ed. 2000, 39, 3558-3588.
6. Evans, D. A.; Trigay, S. W.; Burgey, C. S.; Paras, N. A.; Vojkovsky, T. J. Am. Chem. Soc. 2000, 122, 7936-7943.
7. (a) Dias, L. C. Curr. Org. Chem. 2000, 4, 305-342.
8. (b) Mikami, K.; Shimizu, M. Chem. Rev. 1992, 92, 1021-1050.
9. See, for example: (a) Pignat, K.; Vallotto, J.; Pinna, F.; Strukul, G. Organometallics 2000, 19, 5160-5167.
10. (b) Ghosh, A. K.; Matsuda, H. Org. Lett. 1999, 1, 2157-2159.
11. (c) Oi, S.; Terada, E.; Ohuchi, K.; Kato, T.; Tachibana, Y.; Inoue, Y. J. Org. Chem. 1999, 64, 8660-8667.
12. (d) Blacker, A. J.; Clarke, M. L.; Loft, M. S.; Mahon, M. F.; Williams, J. M. J. Organometallics 1999, 18, 2867-2873.
13. (e) Hori, K.; Kodama, H.; Ohta, T.; Furukawa, I. J. Org. Chem. 1999, 64, 5017-5023.
14. (f) Fujimura, O. J. Am. Chem. Soc. 1998, 120, 10032-10039.
15. (g) Sodeoka, M.; Shibasaki, M. Pure Appl. Chem. 1998, 70, 411-414.
16. (h) Kanemasa, S.; Kanai, T. J. Am. Chem. Soc. 2000, 122, 10710-10711.
17. (i) Hattori, T.; Suzuki, Y.; Uesugi, O.; Oi, S.; Miyano, S. Chem. Commun. 2000, 73-74.
18. Hao, J.; Hatano, M.; Mikami, K. Org. Lett. 2000, 2, 4059-4062.
19. For a Pd catalyzed asymmetric α-imino ester-ene reaction, see: Drury, W. J., III; Ferraris, D.; Cox, C.; Young, B.; Lectka, T. J. Am. Chem. Soc. 1998, 120, 11006-11007.
20. (a) Schmid, R.; Broger, E. A.; Cereghetti, M.; Crameri, Y.; Foricher, J.; Lalonde, M.; Müller, R. K.; Scalone, M.; Schoettel, G.; Zutter, U. Pure Appl. Chem. 1996, 68, 131-138.
21. (b) Schmid, R.; Foricher, J.; Cereghetti, M.; Schönholzer, P. Helv. Chim. Acta 1991, 74, 370-389.
22. As in the Mikami case (footnote 6), the (5)-MeOBiphep ligand provides the (R)-enantiomer of product.
23. 6 are not catalysts under these conditions.
24. For example, see: (a) Evans, D. A.; Murray, J. A.; Matt, P. v.; Norcross, R. D.; Miller, S. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 798-800.
25. (b) Kündig, E. P.; Saudan, C. M.; Bernardinelli, G. Angew. Chem., Int. Ed. 1999, 38, 1220-1223.
26. (a) Cross, R. J. Adv. Inorg. Chem. 1989, 34, 219-292.
27. (b) See also: Johansson, L.; Tilset, M. J. Am. Chem. Soc. 2001, 123, 739-740.
28. For a recent review documenting additive effects in asymmetric catalysis, see: Vogl, E. M.; Gröger, H.; Shibasaki, M. Angew. Chem., Int. Ed. 1999, 38, 1571-1577.
29. Heiberg, H.; Johansson, L.; Gropen, O.; Ryan, O. B.; Swang, O.; Tilset, M. J. Am. Chem. Soc. 2000, 122, 10831-10845.
30. Holtcamp, M. W.; Labinger, J. A.; Bercaw, J. E. J. Am. Chem. Soc. 1997, 119, 848-849.
31. (a) Evans, D. A.; Rovis, T.; Kozlowski, M. C.; Downey, C. W.; Tedrow, J. S. J. Am. Chem. Soc. 2000, 122, 9134-9142.
32. (b) Evans, D. A.; Willis, M. C.; Johnson, J. N. Org. Lett. 1999, 1, 865-868.
33. (c) Evans, D. A.; Rovis, T.; Kozlowski, M. C.; Tedrow, J. S. J. Am. Chem. Soc. 1999, 121, 1994-1995.
34. For recent examples of electronic effects in asymmetric catalysis, see: (a) Murakami, M.; Minamida, R.; Itami, K.; Sawamura, M.; Ito, Y. Chem. Commun. 2000, 2293-2294.
35. (b) RajanBabu, T. V.; Redetich, B.; You, K. K.; Ayers, T. A.; Casalnuovo, A. L.; Calabrese, J. C. J. Org. Chem. 1999, 64, 3429-3447.
36. (c) Schnyder, A.; Togni, A.; Wiesli, U. Organometallics 1997, 16, 255-260.
37. For an example of catalyst immobilization to a silica support by H-bonding of the inflate counterion to acidic surface sites, see: de Rege, F. M.; Morita, D. K.; Ott, K. C.; Tumas, W.; Broene, R. D. Chem. Commun. 2000, 1797-1798.
38. 6OH additives either chemically modify the catalyst or the (complex) counterion, see: (a) Sun, Y.; Metz, M. V.; Stern, C. L.; Marks, T. J. Organometallics 2000, 19, 1625-1627.
39. (b) Ishii, A.; Soloshonok, V. A.; Mikami, K. J. Org. Chem. 2000, 65, 1597-1599.
40. (c) Sato, H.; Tojima, H.; Ikimi, K. J. Mol. Catal. A: Chem. 1999, 144, 285-293.
41. 2, see: Stang, P. J.; Cao, D. H.; Poulter, G. T.; Arif, A. M. Organometallics 1995, 14, 1110-1114.
42. (a) Strauss, S. H. Chem. Rev. 1993, 93, 927-942.
43. (b) Beck, W.; Sünkel, K. Chem. Rev. 1988, 88, 1405-1421.