β-disubstituted allylic chlorides: Substrates for the Cu-catalyzed asymmetric SN2′ reaction

Angewandte Chemie - International Edition

Volumn 45, Issue 36, 2006, Pages 5995-5998

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

^a UNIVERSITY OF GENEVA   (Switzerland)

Author keywords

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

Indexed keywords

CATALYSIS; CATALYST SELECTIVITY; DERIVATIVES; MOLECULAR STRUCTURE; REACTION KINETICS; SUBSTITUTION REACTIONS;

ALLYLIC COMPOUNDS; ASYMMETRIC CATALYSIS; NUCLEOPHILIC SUBSTITUTION;

CHLORINE COMPOUNDS;

EID: 33748784323     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200601855     Document Type: Article

References (53)

1. a) B. M. Trost, C. Lee in Catalytic Asymmetric Synthesis (Ed.: I. Ojima), 2nd ed., Wiley, New York, 2000, p. 593;
2. b) A. Pfaltz, M. Lautens in Comprehensive Asymmetric Catalysis I-HI (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;
4. b) B. M. Trost, J. Org. Chem. 2004, 69, 5813;
5. B. M. Trost, M. L. Crawley, Chem. Rev. 2003, 103, 2921;
6. d) R. Takeuchi, Synlett 2002, 1954.
7. For recent reviews of asymmetric Cu-catalyzed allylic alkylation, see: a) A. Alexakis, C. Malan, L. Lea, K. Tissot-Croset, D. Polet, C. Falciola, Chimia 2006, 60, 124;
8. b) H. Yorimitsu, K. Oshima, Angew. Chem. 2005, 117, 4509;
9. Angew. Chem. Int. Ed. 2005, 44, 4435;
10. c) A. Kar, N. P. Argade, Synthesis 2005, 2995.
11. a) M. Van Klaveren, E. S. M. Persson, A. del Villar, D. M. Grove, J. E. Bäckvall, G. van Koten, Tetrahedron Lett. 1995, 36, 3059;
12. b) A. S. E. Karlstrom, F. F. Huerta, G. J. Meuzelaar, J. E. Bäckvall, Synlett 2001, 923.
13. a) F. Dübner, P. Knochel, Angew. Chem. 1999, 111, 391;
14. Angew. Chem. Int. Ed. 1999, 38, 379;
15. b) F. Dübner, P. Knochel, Tetrahedron Lett. 2000, 41, 9233.
16. a) S. Tominaga, Y. Oi, T. Kato, D. K. An, S. Okamoto, Tetrahedron Lett. 2004, 45, 5585;
17. b) S. Okamoto, S. Tominaga, N. Saimo, K. Kase, K. Shomoda, J. Organomet Chem. 2005, 690, 6001.
18. F. Lopez, A. W. van Zijl, A. J. Minaard, B. L. Feringa, Chem. Commun. 2006, 409.
19. a) K. Tissot-Croset, D. Polet, S. Gille, C. Hawner, A. Alexakis, Synthesis 2004, 2586;
20. b) K. Tissot-Croset, D. Polet, A. Alexakis, Angew. Chem. 2004, 116, 2480;
21. Angew. Chem. Int. Ed. 2004, 43, 2426;
22. c) A. Alexakis, K. Croset, Org. Lett. 2002, 4, 4147;
23. d) A. Alexakis, C. Malan, L. Lea, C. Benhaim, X. Fournioux, Synlett 2001, 927.
24. K. Tissot-Croset, A. Alexakis, Tetrahedron Lett. 2004, 45, 7375.
25. a) H. Malda, A. W. van Zijl, L. A. Arnold, B. L. Feringa, Org. Lett. 2001, 3, 1169;
26. b) A. W. Van Zijl, L. A. Arnold, A. J. Minnaard, B. L. Feringa, Adv. Synth. Catal. 2004, 346, 413.
27. a) U. Piarulli, P. Daubos, C. Claverie, C. Monti, C. Gennari, Eur. J. Org. Chem. 2005, 895;
28. b) U. Piarulli, P. Daubos, C. Claverie, M. Roux, C. Gennari, Angew. Chem. 2003, 115, 244;
29. Angew. Chem. Int. Ed. 2003, 42, 234;
30. c) U. Piarulli, C. Claverie, P. Daubos, C. Gennari, A. J. Minnaard, B. L. Feringa, Org. Lett. 2003, 5, 4493;
31. d) S. Ongeri, U. Piarulli, M. Roux, C. Monti, C. Gennari, Helv. Chim. Acta 2002, 85, 3388.
32. With chiral Schiff base ligands: a) K. E. Murphy, A. H. Hoveyda, Org. Lett. 2005, 7, 1255;
33. b) M. A. Kacprzynski, A. H. Hoveyda, J. Am. Chem. Soc. 2004, 126, 10 676;
34. c) C. A. Luchaco-Cullis, H. Mizutani, K. E. Murphy, A. H. Hoveyda, Angew. Chem. 2001, 113, 1504;
35. Angew. Chem. Int. Ed. 2001, 40, 1456.
36. With chiral NHC ligands: a) J. J. Van Veldhuizen, J. E. Campbell, R. E. Giudici, A. H. Hoveyda, J. Am. Chem. Soc. 2005, 127, 6877;
37. b) A. O. Larsen, W. Leu, C. N. Oberhuber, J. E. Campbell, A. H. Hoveyda, J. Am. Chem. Soc. 2004, 126, 11 130.
38. a) C. Borner, P. J. Goldsmith, S. Woodward, J. Gimeno, S. Gladiali, D. Ramazzoti, Chem. Commun. 2000, 24, 2433;
39. b) K. Biswas, C. Boerner, J. Gimeno, P. J. Goldsmith, D. Ramazzotti, A. L. K. So, S. Woodward, Tetrahedron 2005, 61, 1433;
40. c) P. J. Goldsmith, S. J. Teat, S. Woodward, Angew. Chem. 2005, 117, 2275;
41. Angew. Chem. Int. Ed. 2005, 44, 2235.
42. A. Alexakis, S. Rosset, J. Allamand, S. March, F. Guillen, C. Benhaim, Synlett 2001, 1375.
43. B. L. Feringa, M. Pineschi, L. A. Arnold, R. Imbos, A. H. M. De Vries, Angew. Chem. 1997, 109, 2733;
44. Angew. Chem. Int. Ed. Engl. 1997, 36, 2620.
45. The analogous p-OMe ligands were also tested and gave similar results to L4 (52 % ee), L5 (26 % ee), and L6 (96 % ee).
46. J.-E. Bäckvall, M. Sellén, B. Grant, J. Am. Chem. Soc. 1990, 112, 6615.
47. The Grubbs first-generation catalyst gave poor results.
48. a) H.-J. Gais, H. Müller, J. Bund, M. Scommoda, J. Brandt, G. Raabe, J. Am. Chem. Soc. 1995, 117, 2453;
49. b) J. Bund, H.-J. Gais, S. Erdelmeier, J. Am. Chem. Soc. 1991, 113, 1442.
50. a) P. Schär, P. Renaud, Org. Lett. 2006, 8, 1569;
51. b) E. Nyfeler, P. Renaud, Abstracts of Papers, SCS Fall Meeting 2005, EPFL, Lausanne, Switzerland, October 13, 2005, ORGN-278;
52. c) P. G. Reddy, S. Baskaran, J. Org. Chem. 2004, 69, 3093.
53. For a short review on marine alkaloid synthesis, see: P. Schär, S. Cren, P. Renaud, Chimia 2006, 60, 131.