β- and γ-disubstituted olefins: Substrates for copper-catalyzed asymmetric allylic substitution

Advanced Synthesis and Catalysis

Volumn 350, Issue 7-8, 2008, Pages 1090-1100

  Falciola, Caroline A ^a   Tissot Croset, Karine ^a   Reyneri, Hugo ^a   Alexakis, Alexandre ^a  

^a UNIVERSITY OF GENEVA   (Switzerland)

Author keywords

Allylic alkylation; Allylic compounds; Asymmetric catalysis; Copper; Nucleophilic substitution

Indexed keywords

EID: 53849086179     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/adsc.200800086     Document Type: Article

References (57)

1. a) B. M. Trost, C. Lee, in: Catalytic Asymmetric Synthesis (Ed.: I. Ojima), 2nd edn., Wiley, NewYork, 2000, p 593;
2. b) A. Pfaltz, M. Lautens, in: Comprehensive Asymmetric Catalysis, Vols. I-III, (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Berlin, 1999, p 833.
3. For reviews of asymmetric allylic alkylation with various metals, see: a) H. Miyabe, Y. Takemoto, Synlett 2005, 1641-1655;
4. b) B. M. Trost, J. Org. Chem. 2004, 69, 5813-5837;
5. c) B. M. Trost, M. L. Crawley, Chem. Rev. 2003, 103, 2921-2943;
6. d) R. Takeuchi, Synlett 2002, 1954-1965.
7. For recent reviews of Cu-catalyzed AAA reactions, see: a) C. A. Falciola, A. Alexakis, Eur. J. Org. Chem. 2008, ASAP;
8. b) A. Alexakis, C. Malan, L. Lea, K. Tissot-Croset, D. Polet, C. Falciola, Chimia 2006, 60, 124-130;
9. c) H. Yorimitsu, K. Oshima, Angew. Chem. 2005, 117, 4509-4513;
10. Angew. Chem. Int. Ed. 2005, 44, 4435-4439;
11. d) A. Kar, N. P. Argade, Synthesis 2005, 2995-3022;
12. e) S. A. E. Karlström, J.-E. Böckvall, in: Modern Organocopper Chemistry, (Ed.: N. Krause), Wiley-VCH, Weinheim, 2002.
13. a) M. van Klaveren, E. S. M. Persson, D. M. Grove, J.-E. Böckvall, G. van Koten, Tetrahedron Lett. 1994, 35, 5931-5934;
14. b) A. Alexakis, C. Malan, L. Lea, C. Benhaim, X. Fournioux, Synlett 2001, 927-930;
15. c) F. Lopez, A. W. Van Zijl, A. J. Minnaard, B. L. Feringa, Chem. Commun. 2006, 409-411.
16. a) F. Dubner, P. Knochel, Angew. Chem. 1999, 111, 391-393;
17. Angew. Chem. Int. Ed. 1999, 38, 379-381;
18. b) F. Dubner, P. Knochel, Tetrahedron Lett. 2000, 41, 9233-9237.
19. Allylic substitution on γ-disubstituted allylic substrates, with peptidic Schiff base: a) C. A. Luchaco-Cullis, H. Mizutani, K. E. Murphy, A. H. Hoveyda, Angew. Chem. 2001, 113, 1504-1508;
20. Angew. Chem. Int. Ed. 2001, 40, 1456-1460;
21. with N-heterocyclic diaminocarbenes: b) A. O. Larsen, W. Leu, C. N. Oberhuber, J. E. Campbell, A. H. Hoveyda, J. Am. Chem. Soc. 2004, 126, 11130-11131.
22. a) D. G. Gillingham, A. H. Hoveyda, Angew. Chem. 2007, 119, 3934-3938;
23. Angew. Chem. Int. Ed. 2007, 46, 3860-3864;
24. b) Y. Lee, K. Akiyama, D. G. Gillingham, M. K. Brown, A. H. Hoveyda, J. Am. Chem. Soc. 2008, 130, 446-447.
25. a) C. Borner, P. J. Goldsmith, S. Woodward, J. Gimeno, S. Gladiali, D. Ramazzotti, Chem. Commun. 2000, 2433-2434;
26. b) P. J. Goldsmith, S. J. Teat, S. Woodward, Angew. Chem. 2005, 117, 2275-2277;
27. Angew. Chem. Int. Ed. 2005, 44, 2235-2237.
28. C. A. Falciola, K. Tissot-Croset, A. Alexakis, Angew. Chem. 2006, 118, 6141-6144;
29. Angew. Chem. Int. Ed. 2006, 45, 5995-5998.
30. a) A. Alexakis, S. Rosset, J. Allamand, S. March, F. Guillen, C. Benhaim, Synlett 2001, 1375-1378;
31. b) A. Alexakis, D. Polet, S. Rosset, S. March, J. Org. Chem. 2004, 69, 5660-5667.
32. a) B. L. Feringa, Acc. Chem. Res. 2000, 33, 346-353;
33. b) B. L. Feringa, M. Pineschi, L. A. Arnold, R. Imbos, A. H. M. De Vries, Angew. Chem. 1997, 109, 2733;
34. Angew. Chem. Int. Ed. Engl. 1997, 36, 2620.
35. a) K. Tissot-Croset, D. Polet, A. Alexakis, Angew. Chem. 2004, 116, 2480-2482;
36. Angew. Chem. Int. Ed. 2004, 43, 2426-2428;
37. b) K. Tissot-Croset, D. Polet, S. Gille, C. Hawner, A. Alexakis, Synthesis 2004, 2586-2590;
38. c) D. Polet, A. Alexakis, K. Tissot-Croset, C. Corminboeuf, K. Ditrich, Chem. Eur. J. 2006, 12, 3596-3609;
39. d) K. Tissot-Croset, A. Alexakis, Tetrahedron Lett. 2004, 45, 7375-7378.
40. A. Alexakis, S. El Hajjaji, D. Polet, X. Rathgeb, Org. Lett. 2007, 9, 3393-3395.
41. J.-E. Böckvall, M. Sellén, B. Grant, J. Am. Chem. Soc. 1990, 112, 6615.
42. Ligands L3-L12 were also tested but afforded lower ee values.
43. M. Scommoda, H.-J. Gais, S. Bosshammer, G. Raabe, J. Org. Chem. 1996, 61, 4379-4390.
44. A. Alexakis, K. Croset, Org. Lett. 2002, 4, 4147-4149.
45. The first generation Grubbs catalyst gave poor conversions (<50%).
46. a) J. Bund, H. J. Gais, I. Erdelmeier, J. Am. Chem. Soc. 1991, 113, 1442;
47. b) H.-J. Gais, H. Mueller, J. Bund, M. Scommoda, J. Brandt, G. Raabe, J. Am. Chem. Soc. 1995, 117, 2453.
48. a) P. Schör, P. Renaud, Org. Lett. 2006, 8, 1569;
49. b) E. Nyfeler, P. Renaud, Abstracts of papers, SCS Fall Meeting 2005, EPFL, Lausanne, Switzerland, October 13, 2005, ORGN-278;
50. c) E. Nyfeler, Ph. D. Thesis, University of Berne, 2005;
51. d) E. Nyfeler, P. Schör, P. Renaud unpublished results.
52. P. G. Reddy, S. Baskaran, J. Org. Chem. 2004, 69, 3093-3101.
53. 3) for (R)-2- hexylcyclopentanone; M. M. Kayser, G. Chen, J. D. Stewart, J. Org. Chem. 1998, 63, 7103-7106.
54. L. Palais, I. S. Mikhel, C. Bournaud, L. Micouin, C. A. Falciola, M. Vuagnoux-d'Augustin, S. Rosset, G. Bernardinelli, A. Alexakis, Angew. Chem. 2007, 119, 7606-7609;
55. Angew. Chem. Int. Ed. 2007, 46, 7462-7465.
56. C. A. Falciola, A. Alexakis, Angew. Chem. 2007, 119, 2673-2676;
57. Angew. Chem. Int. Ed. 2007, 46, 2619-2622.