Synthesis and catalytic application of chiral 1,1′-bi-2-naphthol-and biphenanthrol-based pincer complexes: Selective allylation of sulfonimines with allyl stannane and allyl trifluoroborate

Journal of Organic Chemistry

Volumn 72, Issue 13, 2007, Pages 4689-4697

  Aydin, Juhanes ^a   Kumar, K Senthil ^a   Sayah, Mahmoud J ^a   Wallner, Olov A ^a   Szabó, Kálmán J ^a  

^a STOCKHOLM UNIVERSITY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYLATION; BIPHENANTHROLS; SULFONIMINES;

ALCOHOLS; AMINES; CATALYSIS; CATALYST SELECTIVITY; ENANTIOSELECTIVITY; NAPHTHALENE; PALLADIUM; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

DERIVATIVES;

2,2' DIHYDROXY 1,1' BINAPHTHYL; BIPHENANTHROL; BORIC ACID; IMINE; STANNANE; SULFONIMINE DERIVATIVE; TIN; TIN TETRAHYDRIDE; TRIFLUOROBORATE DERIVATIVE; UNCLASSIFIED DRUG;

ALLYLATION; ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; ENANTIOSELECTIVITY; SYNTHESIS;

EID: 34250816839     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo070288b     Document Type: Article

References (54)

1. Trost, B. M.; Lee, C. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; Wiley-VCH: New York, 2000; p 593.
2. Denmark, S. E.; Fu, J. Chem. Rev. 2003, 103, 2763.
3. Trost, B. M.; Vranken, D. L. V. Chem. Rev. 1996, 96, 395.
4. Trost, B. M. Acc. Chem. Res. 1996, 29, 355.
5. Nakamura, H.; Nakamura, K.; Yamamoto, Y. J. Am. Chem. Soc. 1998, 120, 4242.
6. Fernandes, R. A.; Stimac, A.; Yamamoto, Y. J. Am. Chem. Soc. 2003, 125, 14133.
7. Wallner, O. A.; Olsson, V. J.; Eriksson, L.; Szabó, K. J. Inorg. Chim. Acta 2006, 359, 1767.
8. Zanoni, G.; Gladiali, S.; Marchetti, A.; Piccinini, P.; Tredici, I.; Vidari, G. Angew. Chem., Int. Ed. 2004, 43, 846.
9. Hopkins, C. D.; Guan, L.; Malinakova, H. C. J. Org. Chem. 2005, 70, 6848.
10. Malinakova, H. C. Lett. Org. Chem. 2005, 3, 82.
11. Wooten, A. J.; Kim, J. G.; Walsh, P. J. Org. Lett. 2007, 9, 381.
12. Ding, H.; Friestad, G. K. Synthesis 2005, 2815.
13. Alvaro, G.; Savoia, D. Synlett 2002, 651.
14. Taggi, A. E.; Hafez, A. M.; Lectka, T. Acc. Chem. Res. 2003, 36, 10.
15. Wada, R.; Shibuguchi, T.; Makino, S.; Oisaki, K.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2006, 128, 7687.
16. Gastner, T.; Ishitani, H.; Akiyama, R.; Kobayashi, S. Angew. Chem., Int. Ed. 2001, 40, 1896.
17. Ferraris, D.; Dudding, T.; Young, B.; Drudy, W. J.; Lectka, T. J. Org. Chem. 1999, 64, 2168.
18. Fang, X.; Johannsen, M.; Yao, S.; Gathergood, N.; Hazell, R. C.; Jorgensen, K. A. J. Org. Chem. 1999, 64, 4844.
19. Cook, G. R.; Kargbo, R.; Maity, B. Org. Lett. 2005, 7, 2767.
20. Hamada, T.; Manabe, K.; Kobayashi, S. Angew. Chem., Int. Ed. 2003, 42, 3927.
21. Tan, K. L.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2007, 46, 1315.
22. Nakamura, H.; Iwama, H.; Yamamoto, Y. J. Am. Chem. Soc. 1996, 118, 6641.
23. Szabó, K. J. Chem. - Eur. J. 2000, 6, 4413.
24. Wallner, O. A.; Szabó, K. J. Chem. - Eur. J. 2003, 9, 4025.
25. Pichierri, F.; Yamamoto, Y. J. Org. Chem. 2007, 72, 861.
26. Nakamura, H.; Bao, M.; Yamamoto, Y. Angew. Chem., Int. Ed. 2001, 40, 3208.
27. Solin, N.; Narayan, S.; Szabó, K. J. J. Org. Chem. 2001, 66, 1686.
28. Solin, N.; Narayan, S.; Szabó, K. J. Org. Lett. 2001, 3, 909.
29. Méndez, M.; Cuerva, J. M.; Gómez-Bengoa, E.; Cárdenas, D. J.; Echavarren, A. M. Chem. - Eur. J. 2002, 8, 3620.
30. Albrecht, M.; Koten, G. v. Angew. Chem., Int. Ed. 2001, 3750.
31. Dupont, J.; Consorti, C. S.; Spencer, J. Chem. Rev. 2005, 105, 2527.
32. Boom, M. E. v. d.; Milstein, D. Chem. Rev. 2003, 103, 1759.
33. Singleton, J. T. Tetrahedron 2003, 59, 1837.
34. Beletskaya, I. P.; Cheprakov, A. V. J. Organomet. Chem. 2004, 689, 4055.
35. Szabó, K. J. Synlett 2006, 811.
36. Solin, N.; Kjellgren, J.; Szabó, K. J. Angew. Chem., Int. Ed. 2003, 42, 3656.
37. Solin, N.; Kjellgren, J.; Szabó, K. J. J. Am. Chem. Soc. 2004, 126, 7026.
38. Solin, N.; Wallner, O. A.; Szabó, K. J. Org. Lett. 2005, 7, 689.
39. Baber, R. A.; Bedford, R. B.; Betham, M.; Blake, M. E.; Coles, S. J.; Haddow, M. F.; Hurthouse, M. B.; Orpen, A. G.; Pilarski, L. T.; Pringle, P. G.; Wingad, R. L. Chem. Commun. 2006, 3880.
40. Börner, C.; Dennis, M. R.; Sinn, E.; Woodward, S. Eur. J. Org. Chem. 2001, 2435.
41. Cox, P. J.; Wang, W.; Snieckus, V. Tetrahedron Lett. 1992, 33, 2253.
42. Lin, Y.; Chen, C. Terahedron: Asymmetry 1998, 9, 63.
43. Nakajima, M.; Miyoshi, I.; Hashimoto, S.-i. J. Org. Chem. 1999, 64, 2264.
44. Basile, T.; Bocoum, A.; Savoia, D.; Umani-Ronchi, A. J. Org. Chem. 1994, 59, 7766.
45. Sugiura, M.; Mori, C.; Kobayashi, S. J. Am. Chem. Soc. 2006, 128, 11038.
46. Batey, R. A.; Thadani, A. N.; Smil, D. V.; Lough, A. J. Synthesis 2000, 990.
47. Wallner, O. A.; Szabó, K. J. Chem. - Eur. J. 2006, 12, 6976.
48. Johansson, R.; Wendt, O. F. Dalton Trans. 2007, 488.
49. Bedford, R. B.; Draper, S. M.; Scully, P. N.; Welch, S. L. New J. Chem. 2000, 24, 745.
50. Sommer, W. J.; Yu, K.; Sears, J. S.; Ji, Y.; Zheng, X.; Davis, R. J.; Sherrill, C. D.; Jones, C. W.; Weck, M. Organometallics 2005, 24, 4351.
51. Eberhard, M. R. Org. Lett. 2004, 6, 2125.
52. Motoyama, Y.; Narusawa, H.; Nishiyama, N. Chem. Commun. 1999, 131.
53. Motoyama, Y.; Okano, M.; Narusawa, H.; Makihara, N.; Aoki, K.; Nishiyama, H. Organometallics 2001, 20, 1580.
54. Micovic, V. M.; Micovic, M. L. J. J. Org. Chem. 1953, 18, 1190.