Asymmetric allyl- and crotylboration with the robust, versatile, and recyclable 10-TMS-9-borabicyclo[3.3.2]decanes

Journal of the American Chemical Society

Volumn 127, Issue 22, 2005, Pages 8044-8049

  Burgos, Carlos H ^a,b   Canales, Eda ^a   Matos, Karl ^a,c   Soderquist, John A ^a  

^a UNIVERSITY OF PUERTO RICO   (Puerto Rico)

^b MERCK RESEARCH LABORATORIES   (United States)

^c BASF Corporation   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; CHEMICAL REACTIONS; CRYSTALLINE MATERIALS; ESTERS; ISOMERS; MAGNESIUM COMPOUNDS; STEREOCHEMISTRY;

ALLYLATIONS; ALLYLBORATION PROCESS; ENANTIOMERIC ISOMERS; HOMOALLYLIC ALCOHOLS;

ALDEHYDES;

10 TRIMETHYLSILYL BORABICYCLO[3.3.2]DECANE; ALLYLMAGNESIUM BROMIDE; BROMIDE; DECANE; UNCLASSIFIED DRUG;

ALLYLATION; ALLYLBORATION; ARTICLE; ASYMMETRIC SYNTHESIS; CATALYSIS; CHIRALITY; CROTYLBORATION; DRUG ISOLATION; ENANTIOMER; STEREOCHEMISTRY;

ALDEHYDES; ALKANES; ALLYL COMPOUNDS; BICYCLO COMPOUNDS; BORANES; BUTANES; TRIMETHYLSILYL COMPOUNDS;

EID: 20444399909     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja043612i     Document Type: Article

References (71)

1. (a) Herold, T.; Hoffmann, R. W. Angew. Chem., Int. Ed. Engl. 1978, 17. 768.
2. (b) Herold, T.; Schrott, C.; Hoffmann, R. W. Chem. Ber. 1981, 114, 359.
3. (c) Hoffmann, R. W.; Herold, T. Chem. Ber. 1981, 114, 375. See also:
4. See also (d) Ramachandran, P. V. Aldrichimica Acta 2002, 35, 23 and ref. cited therein.
5. (e) Wu, T. R.; Shen, L.; Chong, J. M. Org. Lett. 2004, 6, 2701.
6. (f) Flamme, E. M.; Roush, W. R. J. Am. Chem. Soc. 2002, 124. 13644.
7. (g) Yakelis, N. A.; Roush, W. R. J. Org. Chem. 2003, 68, 3838.
8. (h) Gao, X.; Hall, D. G. J. Am. Chem. Soc. 2003, 125, 9308.
9. (i) Morgan, J. B.; Morken, J. P. Org. Lett. 2003, 5, 2573.
10. (j) Barrett, A. G. M.; Braddock, D. C.; de Koning, P. D.; White, A. J. P.; Williams, D. J. J. Org. Chem. 2000, 65, 375.
11. (k) Barrett, A. G. M.; Beall, J. C.; Braddock, D. C.; Flack, K.; Gibson, V. C.; Salter, M. M. J. Org. Chem. 2000, 65, 6508.
12. (a) Kubota, K.; Leighton, J. L. Angew. Chem., Int. Ed. 2003, 42, 946.
13. (b) Denmark, S. E.; Fu, J. Chem. Rev. 2003, 103, 2763.
14. (c) Waltz, K.; Gavenonis, J.; Walsh, P. J. L. Angew. Chem., Int. Ed. 2001, 41, 3697.
15. (d) Kennedy, J. W. J.; Hall, D. G. J. Org. Chem. 2004, 69, 4412.
16. (e) Ishiyama, T.; Ahiko, T.; Miyaura, N. J. Am. Chem. Soc. 2002, 124, 12414.
17. (f) Wada, R.; Oisaki, K.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2004, 126, 8910.
18. (g) Kim, J. G.; Waltz, K. M.; Garcia, I. F.; Kwiatkowski, D.; Walsh, P. J. J. Am. Chem. Soc. 2004, 126, 12580.
19. (h) Wadamoto, M.; Ozasa, N.; Yanagisawa, A.; Yamamoto, H. J. Org. Chem. 2003, 68, 5593.
20. (a) Yamamoto, Y.; Asoa, N. Chem. Rev. 1993, 93, 2207.
21. (b) Gung, B. W.; Xue, X.; Roush, W. R. J. Am. Chem. Soc. 2002, 124, 10692.
22. (c) Li, Y.; Houk, K. J. Am. Chem. Soc. 1989, 111, 1236.
23. (a) Roush, W. R.; Grover, P. T. J. Org. Chem. 1995, 60, 3806.
24. (a) Brown, H. C.; Racherla, U. S.; Liao Y.; Khanna, V. V. J. Org. Chem. 1992, 57, 6608.
25. (b) Racherla, U.; Liao, Y.; Brown, H. C. J. Org. Chem. 1992, 57, 6614.
26. See, for example: (a) Hoffmann, R. W.; Ladner, W.; Steinbach, K.; Massa, W.; Schmidt, R.; Snatzke, G. Chem. Ber. 1981, 114, 2786.
27. (b) Hoffmann, R. W.; Zeiss, H.-J.; Ladner, W.; Tabche, S. Chem. Ber. 1982, 115, 2357.
28. (c) Hoffmann, R. W.; Endesfeider, A.; Zeiss, H.-J. Carbohydr. Res. 1983, 320.
29. (a) Roush, W. R.; Halterman, R. L. J. Am. Chem. Soc. 1986, 108, 294.
30. (b) Roush, W. R.; Ando, K.; Powers, D. B.; Palkowitz, A. D.; Halterman, R. L. J. Am. Chem. Soc. 1990, 112, 6339.
31. (c) Roush, W. R.; Palkowitz, A. D.; Ando, K. J. Am. Chem. Soc. 1990, 112, 6348.
32. (d) Roush, W. R.; Ando, K.; Powers, D. B.; Halterman, R. L.; Palkowitz, A. D. Tetrahedron Lett. 1988, 44, 5579.
33. (a) Brown, H. C.; Bhat, K. S. J. Am. Chem. Soc. 1986, 108, 293.
34. (b) Brown, H. C.; Racherla, U. S.; Liao, Y.; Khanna, V. V. J. Org. Chem. 1992, 57, 6608.
35. (c) Brown, H. C.; Bhat, K. S.; Randad, R. J. Org. Chem. 1987, 52, 3701.
36. For chiral borolanes. see: Garcia, J.; Kim, B.; Masamune, S. J. Org. Chem. 1987, 52, 4831.
37. (a) Furuta, K.; Mouri, M.; Yamamoto, H. Synlett. 1991, 561.
38. (b) Marshall, J. A.; Tang, Y. Synlett. 1992, 653.
39. (a) Kennedy, J. W.; Hall, D. G. J. Am. Chem. Soc. 2002, 124, 11586.
40. (b) Lachance, H.; Lu, X.; Gravel, M.; Hall, D. G. J. Am. Chem. Soc. 2003, 125, 10160.
41. (a) Hu, T.; Takenaka, N.; Panek, J. S. J. Am. Chem. Soc. 2002, 122, 12806.
42. (b) Masse, C. E.; Panek, J. S. Chem. Rev. 1995, 95, 1293. See also:
43. See also (c) Schaus, J. V.; Jain, N.; Panek, J. S. Tetrahedron 2000, 56, 10263.
44. Hackman, B. M.; Lombardi, P. J.; Leighton, J. L. Org. Lett. 2004, 6, 4375.
45. (a) Yu, W.; Zhang, Y.; Jin, Z. Org. Lett. 2001, 3, 1447.
46. (b) Ley, S. V.; Clase, J. A.; Mansfield, D. J.; Osbor, H. M. I. J. Heterocycles Chem. 1996, 33, 1533.
47. (c) Hoffmann, R. W.; Rolle, U.; Gottlich, R. Liebgs Ann. 1996, 1717.
48. (d) Paterson, I.; Yeung, K.-S.; Ward, R. I.; Cumming, J. G.; Smith, J. D. J. Am. Chem. Soc. 1994, 116, 9391.
49. (e) Patron, A. P.; Richter, P. K.; Tomaszewski, M. J.; Miller, R. A.; Nicolaou, K. C. J. Chem. Soc., Chem. Commun. 1994, 1147.
50. (f) Richter, P. K.; Tomaszewski, M. J.; Miller, R. A.; Patron, A. P.; Nicolaou, K. C. J. Chem. Soc., Chem. Commun. 1994, 1151.
51. (g) Paterson, I.; Britton, R.; Delgado, O.; Meyer, A.; Poullennec, K. G. Angew. Chem., Int. Ed. 2004, 43, 4629.
52. Soderquist, J. A.; Matos, K.; Burgos, C. H.; Lai, C.; Vaquer, J.; Medina. J. R.; Huang, S. D. In ACS Symposium Series 783; Ramachandran, P. V., Brown, H. C., Eds.; American Chemical Society: Washington, DC, 2000; Chapter 13, p 176.
53. Short, R. P.; Masamune, S. J. Am. Chem. Soc. 1989, 111, 1892.
54. (a) Brown, H. C.; Ramachandran, P. V. In Advances in Asymmetric Synthesis; Hassner, A., Ed.; JAI Press: Greenwich, CT, 1995; Vol. 1, p 147.
55. (b) Brown, H. C.; Jadhav, P. K. J. Am. Chem. Soc. 1983, 105, 2092.
56. (c) Brown, H. C.; Jadhav, P. K. J. Org. Chem. 1984, 49, 4089.
57. (d) Wadamoto, M.; Ozasa, N.; Yanagisawa, A.; Yamamoto, H. J. Org. Chem. 1986, 51, 432.
58. (e) Yamasaki, S.; Fujii, K.; Wada, R.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2002, 124, 6536.
59. (f) Soai, K.; Ishizaki, M.; Yokoyama, S. Chem. Lett. 1987, 341.
60. (g) Wu, T. R.; Shen, L.; Chong, J. M. Org. Lett. 2004, 6, 2701.
61. Performed using the Spartan 4.0.4a GL MM program.
62. Omoto, K.; Fujimoto, H. J. Org. Chem. 1998, 63, 8331.
63. Jadhav, P. K.; Bhat, K. S.; Perumal, P. T.; Brown, H. C. J. Org. Chem. 1996, 51, 432.
64. 13C NMR signals for the C-4 position in 9a and 9b were cleanly resolved, appearing at δ 38.5 and 37.6, respectively (δ 35.1 and 35.6 in their Mosher esters).
65. Hoffmann, R. W.; Niels, G.; Schlapback, A. Pure Appl. Chem. 1990, 62, 1993.
66. Fujita, L.; Schlosser, M. Helv. Chim. Acta 1982, 65, 1258.
67. The crotylborane geometry is faithfully reflected in the product alcohols (Table 3). While this is not new, the crotylboration with 10 is much faster than its isomerization, regardless of the reaction temperature. For example, early in the present studies we observed that E-10 produced the β-methyl homoallylic alcohols in a 94:6 anti:syn ratio, both at at 25 and -78 °C. This led us to isolate E-10 and determine its 94:6 E/Z ratio, ultimately optimizing this to ≥98:2 with our modified protocol.
68. For a similar process with terpene-derived reagents, see ref 8b.
69. Dale, J. A.; Mosher, H. S. J. Am. Chem. Soc. 1973, 95, 512.
70. Alexakis, A.; Mutti, S.; Mangeney, P. J. Org. Chem. 1992, 57, 1224.
71. Lai, C.; Soderquist, J. A. Org. Lett. 2005, 7, 799.