Palladium-catalyzed stereoselective allylic alkylation of lithium enolates

Synlett

Volumn , Issue 19, 2005, Pages 2968-2972

  Braun, Manfred ^a   Meier, Thorsten ^a  

^a HEINRICH HEINE UNIVERSITY   (Germany)

Author keywords

Allyl complexes; Asymmetric synthesis; Ketones; Nucleophilic additions; Stereoselectivity

Indexed keywords

1 TETRALONE DERIVATIVE; ACETIC ACID; CARBONIC ACID; CYCLOHEXANONE; CYCLOPENTANONE DERIVATIVE; LITHIUM DERIVATIVE; METAL COMPLEX; PALLADIUM;

ALKYLATION; ALLYLATION; ARTICLE; CATALYSIS; CATALYST; ENANTIOSELECTIVITY; STEREOCHEMISTRY; SUBSTITUTION REACTION;

EID: 28844444584     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-921908     Document Type: Article

References (51)

1. (a) Trost, B. M. Tetrahedron 1977, 33, 2615.
2. (b) Tsuji, J. Organic Synthesis with Palladium Compounds; Springer: New York, 1980.
3. (c) Trost, B. M. Acc. Chem. Res. 1980, 13, 385.
4. (d) Trost, B. M. Pure Appl. Chem. 1981, 53, 2357.
5. (e) Tsuji, J. Pure Appl. Chem. 1982, 54, 197.
6. (f) Godleski, A. In Comprehensive Organic Synthesis, Vol. 4; Trost, B. M., Ed.; Pergamon: Oxford, 1991, 585.
7. For reviews, see: (a) Reiser, O. Angew. Chem., Int. Ed. Engl. 1993, 32, 541;
8. Angew. Chem. 1993, 105, 576.
9. (b) Williams, J. M. J. Synlett 1996, 705.
10. Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395.
11. Helmchen, G. J. Organomet. Chem. 1999, 576, 203.
12. (e) Helmchen, G.; Pfaltz, A. Acc. Chem. Res. 2000, 33, 336.
13. (f) Trost, B. M.; Crawley, M. L. Chem. Rev. 2003, 103, 2921.
14. (g) Trost, B. M. J. Org. Chem. 2004, 69, 5813.
15. Heathcock, C. H. In Modern Synthetic Methods 1992; Scheffold, R., Ed.; VHCA, VCH: Basel, Weinheim, 1992, 1; and references therein.
16. (a) Fiaud, J.-C.; Malleron, J.-L. J. Chem. Soc., Chem. Commun. 1981, 1159.
17. (b) Åkermark, B.; Jutand, A. J. Organomet. Chem. 1981, 217, C41.
18. Negishi, E.; Matsushita, H.; Chatterjee, S.; John, R. A. J. Org. Chem. 1982, 47, 3188.
19. (d) Trost, B. M.; Keinan, E. Tetrahedron Lett. 1980, 21, 2591.
20. (e) Trost, B. M.; Self, C. R. J. Org. Chem. 1984, 49, 468.
21. (a) Review: Kazmaier, U. Curr. Org. Chem. 2003, 7, 317.
22. (b) Trost, B. M.; Schroeder, G. M. J. Am. Chem. Soc. 1999, 121, 6759.
23. Braun, M.; Laicher, F.; Meier, T. Angew. Chem. Int. Ed. 2000, 39, 3494;
24. Angew. Chem. 2000, 112, 3637.
25. You, S.-L.; Hou, X.-L.; Dai, L.-X.; Zhu, X.-Z. Org. Lett. 2001, 3, 149.
26. (a) Kazmaier, U.; Zumpe, F. L. Angew. Chem. Int. Ed. 1999, 38, 1468;
27. Angew. Chem. 1999, 111, 1572.
28. (b) Weiß, T. D.; Helmchen, G.; Kazmaier, U. Chem. Commun. 2002, 1270.
29. (a) Bartels, B.; García-Yebra, C.; Helmchen, G. Eur. J. Org. Chem. 2003, 1097.
30. (b) Peña, D.; Minnaard, A. J.; de Vries, A. H. M.; de Vries, J. G.; Feringa, B. L. Org. Lett. 2003, 5, 475.
31. Takaya, H.; Akutagawa, S.; Noyori, R. Org. Synth. 1988, 67, 20.
32. Takaya, H.; Mashima, K.; Koyano, K. J. Org. Chem. 1986, 51, 629.
33. Seebach, D. Angew. Chem., Int. Ed. Engl. 1988, 27, 1624;
34. Angew. Chem. 1988, 100, 1685.
35. Lloyd-Jones, G. C.; Stephen, S. C.; Fairlamb, I. J. S.; Martorell, A.; Dominguez, B.; Tomlin, P. M.; Murray, M.; Fernandez, J. M.; Jeffery, J. C.; Riis-Johannessen, T.; Guerziz, T. Pure Appl. Chem. 2004, 76, 589.
36. Enders, D. In Asymmetric Synthesis, Part B, Vol. 2; Morrison, J. D., Ed.; Academic Press: New York, 1984, Chap. 4.
37. Imai, M.; Hagihara, A.; Kawasaki, H.; Manabe, K.; Koga, K. Tetrahedron 2000, 56, 179.
38. (a) Burger, E. C.; Tunge, J. A. Org. Lett. 2004, 6, 4113.
39. (b) Behenna, D. C.; Stoltz, B. M. J. Am. Chem. Soc. 2004, 126, 15044.
40. Trost, B. M.; Xu, J. J. Am. Chem. Soc. 2005, 127, 2846.
41. The opposite diastereomer was predominantly obtained in the rearrangement of allyl β-ketoesters: cf. ref. 14a. The product 10 was isolated in 35% yield aside from recovered carbonate 1d (40%). The fact that the latter is non-racemic indicates an at least partial kinetic resolution.
42. (a) Enders, D.; Eichenauer, H. Angew. Chem., Int. Ed. Engl. 1976, 15, 549;
43. Angew. Chem. 1976, 88, 579.
44. (b) Meyers, A. I.; Williams, D. R.; Erickson, G. W.; White, S.; Druelinger, M. J. Am. Chem. Soc. 1981, 103, 3081.
45. Hiroi, K.; Abe, J.; Suya, K.; Sato, S.; Koyama, T. J. Org. Chem. 1994, 59, 203.
46. Yanagisawa, A.; Kikuchi, T.; Kuribayashi, T.; Yamamoto, H. Tetrahedron 1998, 54, 10253.
47. Bordwell, F. G. Acc. Chem. Res. 1988, 21, 456.
48. Braun, M.; Unger, C.; Opdenbusch, K. Eur. J. Org. Chem. 1998, 2389.
49. Hayashi, T.; Yamamoto, A.; Hagihara, T. J. Org. Chem. 1986, 51, 723.
50. Lassaletta, J.-M.; Fernández, R.; Martín-Zamora, E.; Díez, E. J. Am. Chem. Soc. 1996, 118, 7002.
51. R = 26.6 min for (S)-4a; 90% ee.