Enantioselective synthesis of all-carbon quaternary stereogenic centers via copper-catalyzed asymmetric allylic alkylation of (Z)-allyl bromides with organolithium reagents

Chemistry - A European Journal

Volumn 21, Issue 11, 2015, Pages 4209-4212

  Fañanás Mastral, Martín ^a,b   Vitale, Romina ^a   Pérez, Manuel ^a   Feringa, Ben L ^a  

^a UNIVERSITY OF GRONINGEN   (Netherlands)

^b UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

Author keywords

allylic compounds; asymmetric catalysis; copper; organolithium reagents; phosphoramidites

Indexed keywords

ALKYLATION; ALLYLATION; CARBON; CATALYSIS; COPPER; ORGANOMETALLICS; SYNTHESIS (CHEMICAL);

ALLYLIC COMPOUNDS; ASYMMETRIC ALLYLIC ALKYLATIONS; ASYMMETRIC CATALYSIS; ENANTIOSELECTIVE SYNTHESIS; ORGANOLITHIUM REAGENT; PHOSPHORAMIDITES; STEREOGENIC CENTERS; STRUCTURAL MOTIFS;

ENANTIOSELECTIVITY;

EID: 84923693227     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201406006     Document Type: Article

References (59)

1. E. J. Corey, A. Guzman-Perez, Angew. Chem. Int. Ed. 1998, 37, 388-401
2. Angew. Chem. 1998, 110, 402-415
3. J. Christoffers, A. Baro, Angew. Chem. Int. Ed. 2003, 42, 1688-1690
4. Angew. Chem. 2003, 115, 1726-1728
5. C. J. Douglas, L. E. Overman, Proc. Natl. Acad. Sci. USA 2004, 101, 5363-5367
6. B. M. Trost, C. Jiang, Synthesis 2006, 369-396
7. C. Hawner, A. Alexakis, Chem. Commun. 2010, 46, 7295-7306
8. J. P. Das, I. Marek, Chem. Commun. 2011, 47, 4593-4623.
9. C. A. Falciola, A. Alexakis, Eur. J. Org. Chem. 2008, 3765-3780
10. S. Harutyunyan, T. den Hartog, K. Geurts, A. J. Minnaard, B. L. Feringa, Chem. Rev. 2008, 108, 2824-2852
11. A. Alexakis, J. E. Bäckvall, N. Krause, O. Pàmies, M. Diéguez, Chem. Rev. 2008, 108, 2796-2823
12. J.-B. Langlois, A. Alexakis, Top. Organomet. Chem. 2012, 38, 235-268
13. O. Baslé, A. Denicourt-Nowicki, C. Crévisy, M. Mauduit, in Copper-Catalyzed Asymmetric Synthesis (Eds.:, A. Alexakis, N. Krause, S. Woodward,), Wiley-VCH, Weinheim, 2014, Chapter 4.
14. V. Caló, A. Nacci, V. Fiandese, Tetrahedron 1996, 52, 10799-10810
15. N. Harrington-Frost, H. Leuser, M. I. Calaza, F. F. Kneisel, P. Knochel, Org. Lett. 2003, 5, 2111-2114
16. B. Breit, P. Demel, C. Studte, Angew. Chem. Int. Ed. 2004, 43, 3786-3789
17. Angew. Chem. 2004, 116, 3874-3877
18. H. Leuser, S. Perrone, F. Liron, F. F. Kneisel, P. Knochel, Angew. Chem. Int. Ed. 2005, 44, 4627-4631
19. Angew. Chem. 2005, 117, 4703-4707
20. B. Breit, D. Breuninger, Synthesis 2005, 147-157
21. B. Breit, P. Demel, D. Grauer, C. Studte, Chem. Asian J. 2006, 1, 586-597
22. K. Nagao, U. Yokobori, Y. Makida, H. Ohmiya, M. Sawamura, J. Am. Chem. Soc. 2012, 134, 8982-8987
23. C. Feng, Y. Kobayashi, J. Org. Chem. 2013, 78, 3755-3766
24. C. Feng, Y. Kaneko, Y. Kobayashi, Tetrahedron Lett. 2013, 54, 4629-4632.
25. C. A. Luchaco-Cullis, H. Mizutani, K. E. Murphy, A. H. Hoveyda, Angew. Chem. Int. Ed. 2001, 40, 1456-1460
26. Angew. Chem. 2001, 113, 1504-1508
27. M. A. Kacprzynski, A. H. Hoveyda, J. Am. Chem. Soc. 2004, 126, 10676-10681
28. K. E. Murphy, A. H. Hoveyda, Org. Lett. 2005, 7, 1255-1258
29. J. J. Van Veldhuizen, J. E. Campbell, R. E. Giudici, A. H. Hoveyda, J. Am. Chem. Soc. 2005, 127, 6877-6882
30. M. A. Kacprzynski, T. L. May, S. A. Kazane, A. H. Hoveyda, Angew. Chem. Int. Ed. 2007, 46, 4554-4558
31. Angew. Chem. 2007, 119, 4638-4642.
32. F. Gao, K. P. McGrath, Y. Lee, A. H. Hoveyda, J. Am. Chem. Soc. 2010, 132, 14315-14320
33. F. Gao, Y. Lee, K. Mandai, A. H. Hoveyda, Angew. Chem. Int. Ed. 2010, 49, 8370-8374
34. Angew. Chem. 2010, 122, 8548-8552
35. J. A. Dabrowski, F. Gao, A. H. Hoveyda, J. Am. Chem. Soc. 2011, 133, 4778-4781.
36. M. Magrez, Y. Le Guen, O. Baslé, C. Crévisy, M. Mauduit, Chem. Eur. J. 2013, 19, 1199-1203
37. V. Hornillos, M. Pérez, M. Fañanás-Mastral, B. L. Feringa, Chem. Eur. J. 2013, 19, 5432-5441.
38. R. Shintani, K. Takatsu, M. Takeda, T. Hayashi, Angew. Chem. Int. Ed. 2011, 50, 8656-8659
39. Angew. Chem. 2011, 123, 8815-8818
40. B. Jung, A. H. Hoveyda, J. Am. Chem. Soc. 2012, 134, 1490-1493
41. F. Gao, J. L. Carr, A. H. Hoveyda, Angew. Chem. Int. Ed. 2012, 51, 6613-6617
42. Angew. Chem. 2012, 124, 6717-6721
43. K. Hojoh, Y. Shido, H. Ohmiya, M. Sawamura, Angew. Chem. Int. Ed. 2014, 53, 4954-4958
44. Angew. Chem. 2014, 126, 5054-5058.
45. M. Fañanás-Mastral, M. Pérez, P. H. Bos, A. Rudolph, S. R. Harutyunyan, B. L. Feringa, Angew. Chem. Int. Ed. 2012, 51, 1922-1925
46. Angew. Chem. 2012, 124, 1958-1961.
47. M. Pérez, M. Fañanás-Mastral, P. H. Bos, A. Rudolph, S. R. Harutyunyan, B. L. Feringa, Nat. Chem. 2011, 3, 377-381
48. P. H. Bos, A. Rudolph, M. Pérez, M. Fañanás-Mastral, S. R. Harutyunyan, B. L. Feringa, Chem. Commun. 2012, 48, 1748-1750
49. M. Pérez, M. Fañanás-Mastral, V. Hornillos, A. Rudolph, P. H. Bos, S. R. Harutyunyan, B. L. Feringa, Chem. Eur. J. 2012, 18, 11880-11883.
50. C. A. Falciola, A. Alexakis, Chem. Eur. J. 2008, 14, 10615-10627.
51. M. Giannerini, M. Fañanás-Mastral, B. L. Feringa, Nat. Chem. 2013, 5, 667-672
52. M. Giannerini, V. Hornillos, C. Vila, M. Fañanás-Mastral, B. L. Feringa, Angew. Chem. Int. Ed. 2013, 52, 13329-13333
53. Angew. Chem. 2013, 125, 13571-13575
54. V. Hornillos, M. Giannerini, C. Vila, M. Fañanás-Mastral, B. L. Feringa, Org. Lett. 2013, 15, 5114-5117
55. C. Vila, M. Giannerini, V. Hornillos, M. Fañanás-Mastral, B. L. Feringa, Chem. Sci. 2014, 5, 1361-1367.
56. E. Piers, T. Wong, P. D. Coish, C. Rogers, Can. J. Chem. 1994, 72, 1816-1819.
57. N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457-2483.
58. J. F. Teichert, B. L. Feringa, Angew. Chem. Int. Ed. 2010, 49, 2486-2528
59. Angew. Chem. 2010, 122, 2538-2582.