Influence of steric symmetry and electronic dissymmetry on the enantioselectivity in palladium-catalyzed allylic substitutions

Journal of Organic Chemistry

Volumn 68, Issue 8, 2003, Pages 3258-3270

  Vasse, Jean Luc ^a   Stranne, Robert ^a   Zalubovskis, Raivis ^a   Gayet, Carole ^a   Moberg, Christina ^a  

^a ROYAL INSTITUTE OF TECHNOLOGY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYLIC SUBSTITUTIONS;

CATALYSIS; MIXTURES; PALLADIUM; SUBSTITUTION REACTIONS;

ORGANIC COMPOUNDS;

1,3 DIPHENYL 2 PROPENYL ACETATE; 3 CYCLOHEXENYL ACETATE; ACETIC ACID DERIVATIVE; ALLYL COMPOUND; AZEPINE DERIVATIVE; DINAPHTHATODIHYDROAZEPINE DERIVATIVE; DINAPHTHATODIHYDROPHOSPHEPINE DERIVATIVE; LIGAND; PALLADIUM; PHOSPHATE; PHOSPHINE DERIVATIVE; PHOSPHOLANE; PYRROLIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; ELECTROCHEMICAL ANALYSIS; ENANTIOSELECTIVITY; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0037453435     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo026889e     Document Type: Article

References (60)

1. (a) Ojima, I. Catalytic Asymmetric Synthesis; VCH Publishers: New York, 1993.
2. (b) Noyori, R. Asymmetric Catalysis in Organic Synthesis; John Wiley & Sons: New York, 1994.
3. (c) Seyden-Penne, J. Chiral Auxiliaries and Ligands in Asymmetric Synthesis; John Wiley & Sons: New York, 1995.
4. (d) Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H. Comprehensive Asymmetric Catalysis; Springer: Berlin, 1999; Vols. 1-3.
5. Whitesell, J. K. Chem. Rev. 1989, 89, 1581-1590.
6. (a) Frost, C. G.; Howarth, J.; Williams, J. M. J. Tetrahedron: Asymmetry 1992, 3, 1089-1122.
7. (b) Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395-422.
8. (c) Trost, B. M.; Lee, C. In Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; Wiley: New York, 2000; pp 593-649.
9. Saitoh, A.; Misawa, M.; Morimoto, T. Synlett 1999, 483-485.
10. (a) Robert, F.; Gaillard, N.; Sinou, D. J. Mol. Catal. A 1999, 144, 473-476.
11. (b) Robert, F.; Delbecq, F.; Nguefack, C.; Sinou, D. Eur. J. Inorg. Chem. 2000, 351-358.
12. Trost, B. M. Acc. Chem. Res. 1996, 29, 355-364.
13. Stranne, R.; Vasse, J.-L.; Moberg, C. Org. Lett. 2001, 3, 2525-2528.
14. Burk, M. J. Acc. Chem. Res. 2000, 33, 363-372.
15. Bourghida, M.; Widhalm, M. Tetrahedron: Asymmetry 1998, 9, 1073-1083.
16. Guiry, P. J.; McCarthy, M. Tetrahedron 2001, 57, 3809-3844.
17. (a) Burk, M. J.; Feaster, J. E.; Harlow, R. L. Tetrahedron: Asymmetry 1991, 2, 569-592.
18. (b) Morimoto, T.; Ando, N.; Achiwa, K. Synlett 1996, 1211-1212.
19. Burk, M. J.; Pizzano, A.; Martín, J. A.; Liable-Sands, L. M.; Rheingold, A. L. Organometallics 2000, 19, 250-260.
20. (a) Burk, M. J. J. Am. Chem. Soc. 1991, 113, 8518-8519.
21. (b) Burk, M. J.; Feaster, J. E.; Nugent, W. A.; Harlow, R. L. J. Am. Chem. Soc. 1993, 115, 10125-10138.
22. Pichon, M.; Figadère, B. Tetrahedron: Asymmetry 1996, 7, 927-964.
23. Lieser, J. K. Synth. Commun. 1983, 13, 765-767.
24. Brisset, H.; Gourdel, Y.; Pellon, P.; Le Corre, M. Tetrahedron Lett. 1993, 34, 4523-4526.
25. Marinetti, A.; Jus, S.; Labrue, F.; Lemarchand, A.; Genet, J.-P.; Ricard, L. Synthesis 2001, 2095-2104.
26. Gali, H.; Prabhu, K. R.; Karra, S. R.; Katti, K. V. J. Org. Chem. 2000, 65, 676-680.
27. (a) Hall, D. M.; Turner, E. E. J. Chem. Soc. 1955, 1242-1251.
28. (b) Xiao, D.; Zhang, Z.; Zhang, X. Org. Lett. 1999, 1, 1679-1681.
29. Cai, D.; Hugues, D. L.; Verhoeven, T. R.; Reider, P. L. Tetrahedron Lett. 1995, 36, 7991-7994.
30. Boyd, E. A.; Boyd, M. E. K.; Kerrigan, F. Tetrahedron Lett. 1996, 37, 5425-5426.
31. Soulier, E.; Yaouanc, J.-J.; Laurent, P.; des Abbayes, H.; Clément, J.-C. Eur. J. Org. Chem. 2000, 3497-3503.
32. 3: Bitterer, F.; Herd, O.; Kühnel, M.; Stelzer, O.; Weferling, N.; Sheldrick, W. S.; Hahn, J.; Nagel, S.; Rösch, N. Inorg. Chem. 1998, 37, 6408-6417.
33. Chi, Y.; Zhang, X. Tetrahedron Lett. 2002, 43, 4849-4852.
34. (a) Mazaleyrat, J.-P.; Cram, D. J. J. Am. Chem. Soc. 1981, 103, 4585-4586.
35. (b) Mazaleyrat, J.-P. Tetrahedron: Asymmetry 1997, 8, 2709-2721.
36. (a) Hall, D. M.; Lesslie, M. S.; Turner, E. E. J. Chem. Soc. 1950, 711-713.
37. (b) Williams, D. J.; Macy, P. K.; Hezs, D. R. Org. Prep. Proced. Int. 1985, 17, 270-274.
38. Riegel, N.; Darcel, C.; Stéphan, O.; Jugé, S. J. Organomet. Chem. 1998, 567, 219-233.
39. Wimmer, P.; Widhalm M. Tetrahedron: Asymmetry 1995, 6, 657-660.
40. Trost, B. M.; Murphy, D. J. Organometallics 1985, 4, 1143-1145.
41. Yan, Y.-Y.; RajanBabu, T. V. Org. Lett. 2000, 2, 199-202.
42. Lloyd-Jones, G. C.; Stephen, S. C. Chem. Eur. J. 1998, 4, 2539-2549.
43. Trost, B. M.; Bunt, R. C. J. Am. Chem. Soc. 1998, 120, 70-79.
44. Amatore, C.; Jutand, A.; Thuilliez, A. Organometallics 2001, 20, 3241-3249.
45. (a) Mikami, K.; Korenaga, T.; Teruda, M.; Ohkuma, T.; Pham, T.; Noyori, R. Angew. Chem., Int. Ed. 1999, 38,495-497.
46. (b) Mikami, K.; Aikawa, K.; Korenaga, T. Org. Lett. 2001, 3, 243-245.
47. This concept has been used for the design of ligands used in Rh-catalyzed hydroformylations: Nozaki, K.; Sakai, N.; Nanno, T.; Higashijima, T.; Mano, S.; Horiuchi, T.; Takaya, H. J. Am. Chem. Soc. 1997, 119, 4413-4423.
48. (a) Okauchi, T.; Fujita, K.; Ohtaguro, T.; Ohshima, S.; Minami, T. Tetrahedron: Asymmetry 2000, 11, 1397-1403.
49. (b) Evans, D. A.; Campos, K. R.; Tedrow, J. S.; Michael, F. E.; Gagné, M. R. J. Am. Chem. Soc. 2000, 122, 7905-7920.
50. Trost, B. M.; Van Vranken, D. L.; Bingel, C. J. Am. Chem. Soc. 1992, 114, 9327-9343.
51. Amatore, C.; Gamez, S.; Jutand, A. Chem. Eur. J. 2001, 7, 1273-1280.
52. Pfaltz, A. Acc. Chem. Res. 1993, 26, 339-345.
53. Brown, J. M.; Hulmes, D. I.; Guiry, P. J. Tetrahedron 1994, 50, 4493-4506.
54. Hagelin, H.; Åkermark, B.; Norrby, P.-O. Chem. Eur. J. 1999, 5, 902-909.
55. Mackenzie, P. B.; Whelan, J.; Bosnich, B. J. Am. Chem. Soc. 1985, 107, 2046.
56. Saitoh, A.; Achiwa, K.; Tanaka, K.; Morimoto, T. J. Org. Chem. 2000, 65, 4227-4240.
57. Widhalm, M.; Nettekoven, U.; Kalchhauser, H.; Mereiter, K.; Calhorda, M. J.; Félix, V. Organometallics 2002, 21, 315-325.
58. Helmchen, G.; Pfaltz, A. Acc. Chem. Res. 2000, 33, 336-345.
59. This compound has previously been reported (electronic publication in Japanese): Nakada, M. Asahi Garasu Zaidan Josei Kenkyu Seika Hokoku 1998; Chem. Abstr. 1998, 132, 193960.
60. This compound has previously been reported (electronic publication in Japanese): Nakada, M. Asahi Garasu Zaidan Josei Kenkyu Seika Hokoku 1998; Chem. Abstr. 1998, 132, 193960.