Asymmetric addition of chiral boron-ate complexes to cyclic iminium ions

Chemical Science

Volumn 5, Issue 2, 2014, Pages 602-607

  Mohiti, Maziar ^a   Rampalakos, Constantinos ^a   Feeney, Kathryn ^a   Leonori, Daniele ^a   Aggarwal, Varinder K ^a  

^a UNIVERSITY OF BRISTOL   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ASYMMETRIC ADDITION; BORONATE COMPLEXES; BORONIC ESTERS; DIASTEREO-SELECTIVITY; DIASTEREOCONTROL; HETEROCYCLIC STRUCTURES; PYRIDINIUM SALTS; STERIC INTERACTIONS;

BORON; STEREOSELECTIVITY;

SALTS;

EID: 84891465861     PISSN: 20416520     EISSN: 20416539     Source Type: Journal    
DOI: 10.1039/c3sc52409d     Document Type: Article

References (55)

1. (a) J. W. Daly, H. M. Garraffo and T. F. Spande, in Alkaloids: Chemical and Biological Perspectives, ed. S. W. Pelletier, Elsevier, New York, 1999, vol. 13, ch. 1;
2. (b) I. Ojima and D. M. Iula, in Alkaloids: Chemical and Biological Perspectives, ed. S. W. Pelletier, Elsevier, New York, 1999, vol. 13, ch. 5;
3. (c) J. P. Michael, Nat. Prod. Rep., 2008, 25, 166;
4. (d) J. D. Scott and R. M. Williams, Chem. Rev., 2002, 102, 1669.
5. (a) F. Lovering, J. Bikker and C. Humblet, J. Med. Chem., 2009, 52, 6752;
6. (b) F. Lovering, MedChemComm, 2013, 4, 515;
7. (c) D. C. Kombo, K. Tallapragada, R. Jain, J. Chewning, A. A. Mazurov, J. D. Speake, T. A. Hauser and S. Toler, J. Chem. Inf. Model., 2013, 53, 327.
8. (a) J. A. Bull, J. J. Mousseau, G. Pelletier and A. B. Charette, Chem. Rev., 2012, 112, 2642;
9. (b) M. Ahamed and M. H. Todd, Eur. J. Org. Chem., 2010, 5935;
10. (c) M. Chrzanowska and M. Rozwadowska, Chem. Rev., 2004, 104, 3341;
11. (d) A. I. Meyers, D. A. Dickman and M. Boes, Tetrahedron, 1987, 43, 5095;
12. (e) J. Royer, M. Bonin and L. Micouin, Chem. Rev., 2004, 104, 2311.
13. (a) D. L. Comins, H. Hong and J. M. Salvador, J. Org. Chem., 1991, 56, 7197;
14. (b) D. L. Comins, S. P. Joseph, H. Hong, R. S. Al-war, C. J. Foti, Y.-m. Zhang, X. Chen, D. H. LaMunyon and M. Guerra-Weltzien, Pure Appl. Chem., 1997, 69, 477.
15. (a) S. Yamada and M. Ichikawa, Tetrahedron Lett., 1999, 40, 4231;
16. (b) S. Yamada, T. Misono, M. Ichikawa and C. Morita, Tetrahedron, 2001, 7, 5059;
17. (c) S. Yamada and C. Morita, J. Am. Chem. Soc., 2002, 124, 8184.
18. For other C-3 chiral auxiliary-controlled approaches, see: (a) A. I. Meyers, N. R. Natale, D. G. Wettlaufer, S. Raffi and J. Clardy, Tetrahedron Lett., 1981, 22, 5123;
19. (b) A. I. Meyers and T. Oppenlaender, J. Am. Chem. Soc., 1986, 108, 1989;
20. (c) A. Alexakis, P. Mangeney, N. Lensen, J.-P. Tranchier, R. Gosmini and S. Raussou, Pure Appl. Chem., 1996, 68, 531.
21. For other N-chiral auxiliary-based approaches, see: (d) C. E. Hoesl, J. Pabel, K. Polborn and K. T. Wanner, Heterocycles, 2002, 58, 383
22. (e) A. B. Charette, M. Grenon, A. Lemire, M. Pourashraf and J. Martel, J. Am. Chem. Soc., 2001, 123, 11829.
23. For chiral catalyst-controlled approaches, see: (f) E. Ichikawa, M. Suzuki, K. Yabu, M. Albert, M. Kanai and M. Shibasaki, J. Am. Chem. Soc., 2004, 126, 11808;
24. (g) Z. Sun, S. Yu, Z. Ding and D. Ma, J. Am. Chem. Soc., 2007, 129, 9300;
25. (h) M. A. Fernàndez-Ibànez, B. Macià, M. G. Pizzuti, A. J. Minnaard and B. L. Feringa, Angew. Chem., Int. Ed., 2009, 48, 9339;
26. (i) Z. Sun, S. Yu, Z. Ding and D. Ma, J. Am. Chem. Soc., 2007, 129, 9300.
27. For the diastereoselective addition of chiral nucleophiles, see: (j) R. Amann and D. Spitzner, Angew. Chem., Int. Ed., 1991, 30, 1320;
28. (k) M.-L. Bennasar, E. Zulaica, Y. Alonso, B. Vidal, J. T. Vasquez and J. Bosch, Tetrahedron: Asymmetry, 2002, 13, 95;
29. (l) M.-L. Bennasar, E. Zulaica, Y. Alonso, I. Mata, E. Molins and J. Bosch, Chem. Commun., 2001, 1166.
30. For asymmetric chiral auxiliary approaches, see: (a) A. I. Meyers and D. G. Wettlaufer, J. Am. Chem. Soc., 1984, 106, 1135;
31. (b) F. Rezgui, P. Mangeney and A. Alexakis, Tetrahedron Lett., 1999, 40, 6241;
32. (c) S. Yamada and M. Inoue, Org. Lett., 2007, 9, 1477.
33. For asymmetric [1,2]- additions, see: (d) Y. Yamaoka, H. Miyabe and Y. Takemoto, J. Am. Chem. Soc., 2007, 129, 6686.
34. For diastereoselective additions of chiral nucleophiles, see: (a) A. R. Hajipour and M. Hantehzadeh, Phosphorus, Sulfur Silicon Relat. Elem., 2000, 161, 181;
35. (b) R. N. Warrener, L. Liu and R. A. Russell, Chem. Commun., 1997, 2173;
36. (c) M. Chrzanowska, A. Dreas and M. D. Rozwadowska, Tetrahedron: Asymmetry, 2004, 15, 1113.
37. For N-chiral auxiliary-based approaches, see: (d) D. Barbier, C. Marazano, C. Riche, B. C. Das and P. Potier, J. Org. Chem., 1998, 63, 1767.
38. For chiral-catalyst controlled approaches, see: (e) K. Funabashi, H. Ratni, M. Kanai and M. Shibasaki, J. Am. Chem. Soc., 2001, 123, 10784;
39. (f) M. S. Taylor, N. Tokunaga and E. N. Jacobsen, Angew. Chem., Int. Ed., 2005, 44, 6700;
40. (g) K. Frisch, A. Landa, S. Saaby and K. A. Jorgensen, Angew. Chem., Int. Ed., 2005, 44, 6058;
41. (h) I. Liu, Synthesis, 2003, 1705;
42. (i) A. M. Taylor and S. L. Schreiber, Org. Lett., 2006, 8, 143;
43. (j) G. Bergonzini, C. Schindler, C.-J. Wallentin, E. N. Jacobsen and C. Stephenson, Chem. Sci., 2013, DOI: 10.1039/ c3sc52265b.
44. R. Larouche-Gauthier, T. G. Elford and V. K. Aggarwal, J. Am. Chem. Soc., 2011, 133, 16794.
45. The addition of trialkylalkynylboron-ate complexes to N-acyl pyridiniums has been reported but no chiral centres were formed. A. Pelter and K. J. Gould, J. Chem. Soc., Chem. Commun., 1974, 347.
46. The regioselectivity of addition to pyridines activated by chloroformates has been found to be dependent on the nature of the nucleophile. R. Yamaguchi, Y. Nakazono and M. Kawanisi, Tetrahedron Lett., 1983, 24, 1801.
47. The Reissert reaction of 7 (activator: methyl chloroformate) has been reported to be [1,2]-regioselective. E. Ichikawa, M. Suzuki, K. Yabu, M. Albert, M. Kanai and M. Shibasaki, J. Am. Chem. Soc., 2004, 126, 11808.
48. Reviews: (a) J. C. Ma and D. A. Dougherty, Chem. Rev., 1997, 97, 1303;
49. (b) C. A. Hunter, K. R. Lawson, J. Perkins and C. J. Urch, J. Chem. Soc., Perkin Trans. 2, 2001, 651.
50. For cation-p interactions in related systems, see: (c) T. Kawabata, M. Nagato, K. Takasu and K. Fuji, J. Am. Chem. Soc., 1997, 119, 3169;
51. (d) D. L. Comins, S. P. Joseph and R. R. Goehring, J. Am. Chem. Soc., 1994, 119, 4719;
52. (e) R. P. Beckett, V. A. Burgess, S. G. Davies and M. Whittaker, Tetrahedron Lett., 1993, 34, 3617.
53. V. B. Birman, E. W. Uffman, H. Jiang, X. Li and C. J. Kilbane, J. Am. Chem. Soc., 2004, 126, 12226.
54. X. Li, P. Liu, K. N. Houk and V. B. Birman, J. Am. Chem. Soc., 2008, 130, 13836.
55. M. R. Crittall, H. S. Rzepa and D. R. Carbery, Org. Lett., 2011, 13, 1250.