Pd(0) catalyzed asymmetric amination of a prochiral bicyclic allylic diacetate

Tetrahedron

Volumn 54, Issue 35, 1998, Pages 10435-10448

  Muchow, Gunter ^b   Brunel, Jean Michel ^a   Maffei, Michel ^a   Pardigon, Olivier ^a   Buono, Gérard ^a  

^a AIX MARSEILLE UNIVERSITY   (France)

^b ESIM   (France)

Author keywords

[No Author keywords available]

Indexed keywords

2 (ACETOXYMETHYL) 3 (MORPHOLINO METHYLENE)BICYCLO[2.2.1]HEPTA 2,5 DIENE; 2,3 BIS(ACETOXYMETHYL)BICYCLO[2.2.1]HEPTA 2,5 DIENE; ALLYL COMPOUND; AMINE; LIGAND; MORPHOLINE; ORGANOPHOSPHORUS COMPOUND; PALLADIUM; UNCLASSIFIED DRUG;

AMINATION; ARTICLE; CATALYSIS; CHIRALITY; ENANTIOMER; PRIORITY JOURNAL;

EID: 0032572848     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00496-7     Document Type: Article

References (63)

1. 1) (a) Trost, B. M. Tetrahedron 1977, 33, 371
2. (b) Trost, B. M. Acc. Chem. Res. 1980, 13, 385.
3. (c) Trost, B. M. Angew. Chem. Int. Ed. Engl. 1989, 28, 1173.
4. (d) Trost, B. M. Pure Appl. Chem. 1992, 64, 315.
5. (e) Tsuji, J. ; Minami, I. Acc. Chem. Res. 1987, 20, 140.
6. (f) Tsuji, J. Synthesis 1990, 739.
7. (g) Bäckvall, J. E. Acc. Chem. Res. 1983, 16, 335.
8. (h) Bäckvall, J. E. Pure Appl. Chem. 1992, 64, 429.
9. (i) Oppolzer, W. Angew. Chem. Int. Ed. Engl. 1989, 28, 1173.
10. (j) Frost, C. G. ; Howarth, J. ; Williams, J. M. J. Tetrahedron Asymmetry 1992, 3, 1089.
11. (h) Heck, R. F. Palladium Reagents in Organic Syntheses ; Academic Press : London, 1985.
12. (i) Kocovsky, P. Turecek, F. ; Hajicek, J. Synthesis of Natural Products : Problems of Stereoselectivity ; CRC Press : Boca Raton, FL, 1986 ; vol.I and II.
13. (j) Oppolzer, W. Pure Appl. Chem. 1988, 60, 39 and 1990, 62, 1941.
14. (j) Oppolzer, W. Pure Appl. Chem. 1988, 60, 39 and 1990, 62, 1941.
15. (k) Hosokawa, S. Acc. Chem. Res. 1990, 23, 49.
16. 2) (a) Trost, B. M. ; van Vranken, D. L. Chem. Rev. 1996, 96, 395-422.
17. (b) Trost, B. M. ; Organ, M. G. ; O'doherty, G. A. J. Am. Chem. Soc. 1995, 117, 9662-9670.
18. (c) Bolm, C. ; Kaufmann, D. ; Gessler, S. ; Harms, K. J. Organomet. Chem. 1995, 502, 47-52.
19. (d) Seebach, D. ; Devaquet, E ; Ernst, A. ; Hayakawa, M. ; Kühnle, F. N. M. ; Schweizer, W. B. ; Weber, B. Helv. Chim. Acta 1995, 78, 1636-1650.
20. (e) von Matt, P. ; Pfaltz, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 566-569.
21. (f) Sprinz, J.; Helmchen, G. Tetrahedron Lett. 1993, 34, 1769-1773.
22. (g) Dawson, G. J. ; Frost, C. G. ; Williams, J. M. J. ; Coote, S. J. Tetrahedron Lett. 1993, 34, 3149-3150.
23. 3) (a) Atkins, K. E.; Walker, W. E.; Manyik, R. M. Tetrahedron Lett. 1970, 3821.
24. (b) Trost, B. M.; Gedleski, S. A.; Genêt, J. P. J. Am. Chem. Soc. 1978, 700, 3930.
25. (c) Bäckvall, J. E.; Nordberg, R. E.; Nyström, J. E.; Hogberg, T.; Ulff B. J. Org. Chem. 1981, 46, 3479.
26. (d) Tanígawa, Y.; Nishimura, K.; Murahashi, S. I. Tetrahedron Lett. 1982, 5549.
27. (e) Tanikaga, R.; Tagouchi, J.; Takya, M.; Kaji, A. J. Chem. Soc., Chem. Commun., 1987, 386.
28. 4) (a) Nordberg, R. E. ; Bäckvall, J. E. J. Organomet. Chem. 1985, 285, C24-C26.
29. (b) Blart, E. ; Genêt, J. P. ; Safi, M. ; Savignac, M. ; Sinou, D. Tetrahedron 1994, 50, 505.
30. 5) (a) Yoshizaki, H. ; Satoh, H. ; Sato, Y. ; Nukui, S. ; Shibasaki, M. ; Mori, M. J. Org. Chem. 1995, 60, 2016.
31. (b) Genêt, J. P. ; Thorimbert, S. ; Touzin, A. M. Tetrahedron Lett. 1993, 34, 1159.
32. 6) (a) Hayashi, T. ; Yamamoto, A. ; Ito, Y. ; Nishioka, E. ; Miura, H. ; Yanagi, K. J. Am. Chem. Soc. 1989, 111, 6301.
33. (b) Trost, B. M. ; Van Vranken, D. L. J. Am. Chem. Soc. 1993, 115, 444.
34. (c) Togni, A. ; Burkhardt, U. ; Gramlich, V. ; Pregosin, P. S. ; Salzmann, R. J. Am. Chem. Soc. 1996, 118, 1031.
35. (d) Von Matt, P. ; Loiseleur, O. ; Koch, G. ; Pfaltz, A. ; Lebefer, C. ; Feucht, T. ; Helmchen, G. Tetrahedron Asymmetry 1994, 5, 573.
36. (e) Blöchl, P. E. ; Togni, A. Organometallics 1996, 15, 4125.
37. (f) Burkhardt, U. ; Baumann, M. ; Trabesinger, G. ; Gramlich, V. ; Togni, A. Organometallics 1997, 16, 5252.
38. 7) Muchow, G. ; Brunel, J. M. ; Maffei, M. ; Buono, G. J. Org. Chem. 1995, 60, 852.
39. 8) Ranchoux, M. ; Brunel, J. M. ; Iacazio, G. ; Buono, G. Tetrahedron Asymmetry 1998, 9, 581.
40. 9) (a) Jones, J. B. Tetrahedron 1986, 42, 3351.
41. (b) Santaniello, E. ; Ferraboschi, P. ; Grisenti, P. ; Manzocchi, A. Chem. Rev. 1992, 92, 1071.
42. (c) Azerad, R. Bull. Soc. Chim. Fr. 1995, 132, 17.
43. (d) Maezaki, N. ; Soejima, M. ; Takeda, M. ; Sakamoto, A. ; Matsumori, Y. ; Tanaka, T. ; Iwata, C. Tetrahedron 1996, 19, 6527.
44. (e) Fujioka, H. ; Nagatomi, Y. ; Kitagawa, H. ; Kita, Y. J. Am. Chem. Soc. 1997, 119, 12016 and references cited therein.
45. 10) It is noteworthy that in absence of catalyst, no conversion occurred.
46. 11) Genêt, J. P.; Balabane, M.; Bäckvall, J. E.; Nyström, J. E. Tetrahedron Lett. 1983, 2745.
47. 3 and diethyl amine as nucleophile did not lead to the expected diaminated compound 3a probing the low reactivity of the system towards a second nucleophilic attack.
48. 13) Yamamoto, T.; Akimoto, M.; Saito, O.; Yamamoto, A. Organometallics 1986, 5, 1559.
49. 14) Åkermark, B.; Zetterberg, K. Tetrahedron Lett. 1975, 43, 3733.
50. 4 on allyl chloride or acetate and that this complex was responsible for the observed enhanced electrophilicity of the allyl substrate. Trost, B. M.; Weber, L.; Strege, P. E.; Fullerton, T. J.; Dietsche, T. J. J. Am. Chem. Soc. 1978, 100, 3401.
51. (b) Attempts to isolate the π-allyl palladium (II) complex from diacetate 1 according to Hayashi's method gave no results. Hayashi, T.; Hagibara, T.; Komishi, M.; Kumada, M. J. Am. Chem. Soc. 1983, 105, 7767.
52. 16) (a) Tolman, C. A. Chem. Rev. 1977, 77, 313;
53. (b) Bartik, T.; Himmler, T.; Schulte, H. G.; Seevogel, K. J. Organomet. Chem. 1984, 272, 29.
54. 17) Giering, W. P. ; Rahmaan, M. M. ; Liu, H. Y. ; Erics, K. ; Prock, A. Organometallics 1989, 8, 1.
55. 18) (a) Cros, P. ; Buono, G. ; Peiffer, G. ; Denis, D. ; Mortreux, A. ; Petit, F. New. J. Chem. 1987, 11, 573.
56. (b) Arzoumanian, H. ; Buono, G. ; Choukrad, M'B. ; Petrignani, J. F. Organometallics 1988, 7, 59.
57. (c) Pardigon, O. ; Buono, G. Tetrahedron : Asymmetry 1993, 3, 2427.
58. 19) Brunel, J. M. ; Chiodi, O. ; Faure, B. ; Fotiadu, F. ; Buono, G. J. Organomet. Chem. 1997, 529, 285
59. 20) Brunel, J. M. ; Constantieux, T. ; Labande, A. ; Lubatti, F. ; Buono, G. Tetrahedron Lett. 1997, 34, 5971.
60. 21) Brunel, J. M. ; Pardigon, O. ; Maffei, M. ; Buono, G. Tetrahedron : Asymmetry 1992, 10, 1243.
61. nd edition, Pergamon Press, Oxford, 1980.
62. 23) Coulson, D. R. Inorg. Synth. 1972, 13, 121.
63. 24) Ukai, T. ; Kawazawa, H. ; Ishii, Y. ; Bonnett, J. J. ; Ibers, J. A. J. Organomet. Chem. 1974, 65, 253.