Hydroboration. 93. Convenient conversion of optically pure 2-organylapopinenes into the (2-organylapoisopinyl)dihaloboranes potentially valuable for asymmetric synthesis via chiral organoboranes

Organometallics

Volumn 15, Issue 16, 1996, Pages 3504-3508

  Dhokte, Ulhas P ^a   Brown, Herbert C ^a  

^a PURDUE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0011913957     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om960240g     Document Type: Article

References (57)

1. Brown, H. C.; Zweifel, G. J. Am. Chem. Soc. 1961, 83, 486.
2. (a) Brown, H. C.; Singaram, B. Acc. Chem. Res. 1988, 21, 287.
3. (b) Matteson, D. S. Synthesis 1986, 973.
4. (c) Brown, H. C.; Ramachandran, P. V. Pure Appl. Chem. 1991, 63, 307.
5. (d) Brown, H. C.; Ramachandran, P. V. In Advances in Asymmetric Synthesis; Hassner, A., Ed.; JAI press: Greenwich, CT, 1995; Vol. 1, pp 147-210.
6. (a) Brown, H. C.; Yoon, N. M. J. Am. Chem. Soc. 1977, 99, 5514.
7. (b) Midland, M. M.; Greer, S.; Tramontano, A.; Zderic, S. A. J. Am. Chem. Soc. 1979, 101, 2352.
8. (c) Brown, H. C.; Jadhav, P. K.; Mandal, A. K. J. Tetrahedron 1981, 37, 3547.
9. (d) Brown, H. C.; Desai, M. C.; Jadhav, P. K. J. Org. Chem. 1982, 47, 5065.
10. (e) Brown, H. C.; Jadhav, P. K.; Mandal, A. K. J. Org. Chem. 1982, 47, 5074.
11. (a) Brown, H. C.; Ramachandran, P. V.; Teodorović, A.; Swaminathan, S. Tetrahedron Lett. 1991, 32, 6691.
12. (b) Brown, H. C.; Srebnik, M. S.; Ramachandran, P. V. J. Org. Chem. 1989, 54, 1577.
13. (c) Brown, H. C.; Ramachandran, P. V. Acc. Chem. Res. 1992, 25, 16.
14. (a) Brown, H. C.; Jadhav, P. K. J. Am. Chem. Soc. 1983, 105, 2092.
15. (b) Brown, H. C.; Jadhav, P. K.; Perumal, P. T. Tetrahedron Lett. 1984, 25, 5111.
16. (c) Brown, H. C.; Jadhav, P. K. Tetrahedron Lett. 1984, 25, 1215.
17. (d) Jadhav, P. K.; Bhat, K. S.; Perumal, P. T.; Brown, H. C. J. Org. Chem. 1986, 51, 432.
18. (e) Brown, H. C.; Bhat, K. S. J. Am. Chem. Soc. 1986, 108, 5919.
19. (f) Racherla, U. S.; Brown, H. C. J. Org. Chem., 1991, 56, 401.
20. (a) Joshi, N. N.; Srebnik, M.; Brown, H. C. J. Am. Chem. Soc. 1988, 110, 6246.
21. (b) Srebnik, M.; Joshi, N. N.; Brown, H. C. Isr. J. Chem. 1989, 29, 229.
22. (a) Matteson, D. S.; Majumdar, D. J. Am. Chem. Soc. 1980, 102, 7588
23. (b) Matteson, D. S.; Majumdar, D. Organometallics 1983, 2, 1529
24. (c) Matteson, D. S.; Sadhu, K. M.; Peterson, M. L. J. Am. Chem. Soc. 1986, 108, 810.
25. (d) Brown, H. C.; Singh, S. M.; Rangaishenvi, M. V. J. Org. Chem. 1986, 51, 3150.
26. (e) Brown, H. C.; Rangaishenvi, M. V. J. Organomet. Chem. 1988, 358, 15.
27. (f) Matteson, D. S. Pure Appl. Chem. 1991, 63, 339.
28. (a) Paterson, I.; Goodman, J. M.; Lister, M. A. Schumann, R. C.; McClure, C. K.; Norcross, R. D. Tetrahedron Lett. 1990, 46, 4663.
29. (b) Paterson, I. Pure Appl. Chem. 1992, 64, 1821.
30. (a) Houk, K. N.; Rondan, N. G.; Wu, Y.-D.; Metz, J. T. Paddon-Row, M. N. Tetrahedron 1984, 40, 2257.
31. (b) Egger, M.; Keese, R. Helv. Chim. Acta 1987, 70, 1843.
32. Brown, H. C.; Randad, R. S.; Bhat, K. S.; Zaidlewicz, M.; Wiessman, S. A.; Jadhav, P. K.; Perumal, P. T. J. Org. Chem. 1988, 53, 5513.
33. (a) Brown, H. C.; Ramachandran, P. V.; Weissman, S. A.; Swaminathan, S. J. Org. Chem. 1990, 55, 6328.
34. (b) Ramachandran, P. V.; Brown, H. C.; Swaminathan, S. Tetrahedron Asymm. 1990, 1, 433.
35. Brown, H. C.; Dhokte, U. P. J. Org. Chem. 1994, 59, 2025.
36. Brown, H. C.; Weissman, S. A.; Perumal, P. T.; Dhokte, U. P. J. Org. Chem. 1990, 55, 1217.
37. Dhokte, U. P.; Brown, H. C. Tetrahedron Lett. 1994, 35, 4715.
38. (a) Brown, H. C.; Mahindroo, V. K.; Dhokte U. P. J. Org. Chem. 1996, 61, 1609.
39. (b) Dhokte, U. P.; Kulkarni, S. V.; Brown, H. C. J. Org. Chem. 1996, 61, 0000.
40. (a) Hawkins, J. M.; Loren, S. J. Am. Chem. Soc. 1991, 113, 7794.
41. (b) Hawkins, J. M.; Loren, S.; Nambu, M. J. Am. Chem. Soc. 1994, 116, 1657.
42. (a) Bir, G.; Kaufmann, D. J. Organomet. Chem. 1990, 390, 1.
43. (b) Bir, G.; Kaufmann, D. Tetrahedron Lett. 1987, 28, 777.
44. (a) Soundararajan, R.; Matteson, D. S. J. Org. Chem. 1990, 55, 2274.
45. 19b
46. Brown, H. C.; Salunkhe, A. M.; Argade, A. B. Organometallics 1992, 11, 3094 and references cited therein.
47. Brown, H. C.; Singaram, B. J. Am. Chem. Soc. 1984, 106, 1797.
48. Brown, H. C.; Cole, T. E.; Singaram, B. Organometallics 1984, 3, 774.
49. Brown, H. C.; Salunkhe, A. M.; Singaram, B. J. Org. Chem. 1991, 56, 1170.
50. (a) Brown, H. C.; Ravindran, N. J. Org. Chem. 1977, 42, 2533.
51. (b) Brown, H. C.; Kulkarni, S. U. J. Organomet. Chem. 1982, 239, 23.
52. Brown, H. C.; Ramachandran, P. V.; Chandrasekharan, J. Heteroatom Chem. 1995, 6, 117.
53. Brown, H. C.; Dhokte, U. P. J. Org. Chem. 1994, 59, 5479.
54. (a) Westley, J. W.; Halpern, B. J. J. Org. Chem. 1968, 33, 3978.
55. (b) Dale, J. A.; Dull, D. L.; Mosher, H. S. J. Org. Chem. 1969, 34, 2543.
56. Brown, H. C.; Kramer, G. W.; Levy, A. B.; Midland, M. M. Organic Synthesis via Boranes; Wiley-Interscience: New York, 1975.
57. Brown, H. C.; Dhokte, U. P. J. Org. Chem. 1994, 59, 2365.