Lewis and Brønsted acid catalyzed allylboration of carbonyl compounds: From discovery to mechanism and applications

Synlett

Volumn , Issue 11, 2007, Pages 1644-1655

  Hall, Dennis G ^a  

^a UNIVERSITY OF ALBERTA   (Canada)

Author keywords

Allylations; Boron; Catalysis; Lewis acids; Stereoselectivity

Indexed keywords

ALDEHYDE DERIVATIVE; ALLYL COMPOUND; BORONIC ACID DERIVATIVE; BRONSTED ACID; CARBONYL DERIVATIVE; LEWIS ACID; SILICON; TIN; TITANIUM;

ALLYLATION; ARTICLE; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; ENANTIOSELECTIVITY; NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; STOICHIOMETRY;

EID: 34447549207     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-980384     Document Type: Article

References (73)

1. (a) Denmark, S. E.; Almstead, N. G. In Modern Carbonyl Chemistry; Otera, J., Ed.; Wiley-VCH: Weinheim, 2000, Chap. 10, 299-402.
2. (b) Chemler, S. R.; Roush, W. R. In Modern Carbonyl Chemistry; Otera, J., Ed.; Wiley-VCH: Weinheim, 2000, Chap. 11, 403-490.
3. Denmark, S. E.; Fu, J. Chem. Rev. 2003, 103, 2763.
4. (a) Kennedy, J. W. J.; Hall, D. G. In Boronic Acids; Hall, D. G., Ed.; Wiley-VCH: Weinheim, 2005, Chap. 6, 241-277.
5. (b) Lachance, H.; Hall, D. G. In Organic Reactions; Overman, L. E., Ed.; Wiley: New York, 2007, in press.
6. Mikhailov, B. M.; Bubnov, Y. N. Izv. Akad. Nauk. SSSR, Ser. Khim. 1964, 1874;
7. Chem. Abstr. 1965, 62, 11840e.
8. Favre, E.; Gaudemar, M. C. C. R. Seances Acad. Sci., Ser. C 1966, 263, 1543.
9. (a) Hoffmann, R. W.; Zeiss, H.-J. Angew. Chem., Int. Ed. Engl. 1979, 18, 306.
10. (b) Hoffmann, R. W.; Zeiss, H.-J. J. Org. Chem. 1981, 46, 1309.
11. (a) Brown, H. C.; Jadhav, P. K. J. Am. Chem. Soc. 1983, 105, 2092.
12. (b) Brown, H. C.; Bhat, K. S. J. Am. Chem. Soc. 1986, 108, 293.
13. (c) Ramachandran, P. V. Aldrichimica Acta 2002, 35, 23.
14. (a) Garcia, J.; Kim, B.; Masamune, S. J. Org. Chem. 1987, 52, 4831.
15. (b) Short, R. P.; Masamune, S. J. Am. Chem. Soc. 1989, 111, 1892.
16. (a) Corey, E. J.; Yu, C.-M.; Kim, S. S. J. Am. Chem. Soc. 1989, 111, 5495.
17. (b) Corey, E. J.; Yu, C.-M.; Lee, D.-H. J. Am. Chem. Soc. 1990, 112, 878.
18. (a) Roush, W. R.; Walts, A. E.; Hoong, L. K. J. Am. Chem. Soc. 1985, 107, 8186.
19. (b) Roush, W. R.; Ando, K.; Powers, D. B.; Palkowitz, A. D.; Halterman, R. L. J. Am. Chem. Soc. 1990, 112, 6339.
20. (a) Burgos, C. H.; Canales, E.; Matos, K.; Soderquist, J. A. J. Am. Chem. Soc. 2005, 127, 8044.
21. (b) Lai, C.; Soderquist, J. A. Org. Lett. 2005, 7, 799.
22. (c) Canales, E.; Prasad, K. G.; Soderquist, J. A. J. Am. Chem. Soc. 2005, 127, 11572.
23. Denmark, S. E.; Weber, E. J. Helv. Chim. Acta 1983, 66, 1655.
24. (a) Li, Y.; Houk, K. N. J. Am. Chem. Soc. 1989, 111, 1236.
25. (b) Gennari, C.; Fioravanzo, E.; Bernardi, A.; Vulpetti, A. Tetrahedron 1994, 50, 8815.
26. (c) Vulpetti, A.; Gardner, M.; Gennari, C.; Bernardi, A.; Goodman, J. M.; Paterson, I. J. Org. Chem. 1993, 1711.
27. (d) Omoto, K.; Fujimoto, H. J. Org. Chem. 1998, 63, 8331.
28. (e) Gajewski, J. J.; Bocian, W.; Brichford, N. L.; Henderson, J. L. J. Org. Chem. 2002, 67, 4236.
29. Pratt, A. J.; Thomas, E. J. J. Chem. Soc., Chem. Commun. 1982, 1115.
30. More recently, crotyltrichlorosilane reagents have also been shown to react diastereospecifically, presumably through a cyclic transition state of Type I. Despite their high efficiency with aromatic aldehydes and α,β-unsaturated aldehydes, allyl- and crotylsilylation methods based on chiral phosphoramide catalysts are incompatible with aliphatic aldehydes: (a) Denmark, S. E.; Fu, J. J. Am. Chem. Soc. 2001, 123, 9488.
31. (b) Denmark, S. E.; Fu, J. Chem. Commun. 2003, 167.
32. (a) Kennedy, J. W. J.; Hall, D. G. J. Am. Chem. Soc. 2002, 124, 898.
33. (b) Zhu, N.; Hall, D. G. J. Org. Chem. 2003, 68, 6066.
34. Kennedy, J. W. J.; Hall, D. G. J. Am. Chem. Soc. 2002, 124, 11586.
35. Ishiyama, T.; Ahiko, T.-a.; Miyaura, N. J. Am. Chem. Soc. 2002, 124, 12414.
36. Kennedy, J. W. J.; Hall, D. G. J. Org. Chem. 2004, 69, 4412.
37. Yu, S.-H.; Ferguson, M. J.; McDonald, R.; Hall, D. G. J. Am. Chem. Soc. 2005, 127, 12808.
38. (a) Carroll, A. R.; Taylor, W. C. Aust. J. Chem. 1991, 44, 1615.
39. (b) Carroll, A. R.; Taylor, W. C. Aust. J. Chem. 1991, 44, 1705.
40. (a) Hong, S.-p.; McIntosh, M. C. Org. Lett. 2002, 4, 19.
41. (b) Hutchison, J. M.; Hong, S.-p.; McIntosh, M. C. J. Org. Chem. 2004, 69, 4185.
42. (c) Gurjar, M. K.; Cherian, J.; Ramana, C. V. Org. Lett. 2004, 6, 317.
43. (d) Coleman, R. S.; Gurrala, S. R. Org. Lett. 2004, 6, 4025.
44. Elford, T.; Yu, S. H.; Arimura, Y.; Hall, D. G. J. Org. Chem. 2007, 72, 1276.
45. (a) Kabalka, G. W.; Venkataiah, B.; Dong, G. J. Org. Chem. 2004, 69, 5807.
46. (b) Kabalka, G. W.; Venkataiah, B.; Dong, G. Tetrahedron Lett. 2005, 46, 4209.
47. Kabalka, G. W.; Venkataiah, B. Tetrahedron Lett. 2005, 46, 7325.
48. (a) Ramachandran, P. V.; Pratihar, D.; Biswas, D.; Srivastava, A.; Reddy, M. V. R. Org. Lett. 2004, 6, 481.
49. (b) Ramachandran, P. V.; Pratihar, D.; Biswas, D. Org. Lett. 2006, 8, 3877.
50. Selander, N.; Sebelius, S.; Estay, C.; Szabó, K. J. Eur. J. Org. Chem. 2006, 4085.
51. Rauniyar, V.; Hall, D. G. J. Am. Chem. Soc. 2004, 126, 4518.
52. Brown, H. C.; Racherla, U. S.; Pellechia, P. J. J. Org. Chem. 1990, 55, 1868.
53. Lachance, H.; Lu, X.; Gravel, M.; Hall, D. G. J. Am. Chem. Soc. 2003, 125, 10160.
54. (a) Hoffmann, R. W.; Herold, T. Angew. Chem., Int. Ed. Engl. 1978, 18, 768.
55. (b) Herold, T.; Schrott, U.; Hoffmann, R. W. Chem. Ber. 1981, 111, 359.
56. Gravel, M.; Lachance, H.; Lu, X.; Hall, D. G. Synthesis 2004, 1290.
57. Faveau, C.; Mondon, M.; Gesson, J.-P.; Mahnke, T.; Gebhardt, S.; Koert, U. Tetrahedron Lett. 2006, 47, 8305.
58. (a) Pihko, P. M. Angew. Chem. Int. Ed. 2004, 43, 2062.
59. (b) Bolm, C.; Rantanen, T.; Schiffers, I.; Zani, L. Angew. Chem. Int. Ed. 2005, 44, 1758.
60. Yamamoto, H.; Futatsugi, K. Angew. Chem. Int. Ed. 2005, 44, 1924.
61. (a) Ishihara, K.; Kaneeda, M.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 11179.
62. (b) Nakamura, S.; Kaneeda, M.; Ishihara, K.; Yamamoto, H. J. Am. Chem. Soc. 2000, 122, 8120.
63. (c) Ishihara, K.; Nakamura, S.; Kaneeda, M.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 12854.
64. (d) Ishihara, K.; Nakamura, S.; Yamamoto, H. J. Org. Chem. 1998, 63, 6444.
65. (e) Ishihara, K.; Nakashima, D.; Hiraiwa, Y.; Yamamoto, H. J. Am. Chem. Soc. 2003, 125, 24.
66. Rauniyar, V.; Hall, D. G. Angew. Chem. Int. Ed. 2006, 45, 2426.
67. Wada, R.; Oisaki, K.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2004, 126, 8910.
68. Lou, S.; Moquist, P. N.; Schaus, S. E. J. Am. Chem. Soc. 2006, 128, 12660.
69. (a) Hoffmann, R. W. Pure Appl. Chem. 1988, 60, 123.
70. (b) Hoffmann, R. W.; Niel, G.; Schlapbach, A. Pure Appl. Chem. 1990, 62, 1993.
71. Hoffmann, R. W.; Weidmann, U. J. Organomet. Chem. 1980, 195, 137.
72. Carosi, L.; Lachance, H.; Hall, D. G. Tetrahedron Lett. 2005, 46, 8981.
73. Feng, P.; Hall, D. G. J. Am. Chem. Soc. 2007, 129, 3070.