Hydroboration. 62. Monoisopinocampheylborane, an Excellent Chiral Hydroborating Agent for Trans-Disubstituted and Trisubstituted Alkenes. Evidence for a Strong Steric Dependence in Such Asymmetric Hydroborations

Journal of Organic Chemistry

Volumn 47, Issue 26, 1982, Pages 5074-5083

  Brown, Herbert C ^a   Jadhav, Prabhakar K ^a   Mandal, Arun K ^a  

^a PURDUE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001496991     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00147a006     Document Type: Article

References (20)

1. Brown, H. C. “Boranes in Organic Chemistry”; Cornell University Press: Ithaca, NY, 1972.
2. Brown, H. C.; Kramer, G. W.; Levy, A. B.; Midland, M. M. “Organic Syntheses via Boranes”; Wiley-Interscience: New York, 1975.
3. Pasto, D. J. In “Boron Hydride Chemistry”; Mutterties, E. L., Ed.; Academic Press: New York, 1975.
4. Pelter, A.; Smith, K. In “Comprehensive Organic Chemistry”; Barton, D. H. R.; Ollis, W. D.; Pergamon Press: Oxford, 1979; Vol. 3.
5. Brown, H. C.; Zweifel, G. J. Am. Chem. Soc. 1961, 83, 486.
6. For a recent review on “Asymmetric Syntheses via Chiral Organoborane Reagents”, see:
7. Brown, H. C.; Jadhav, P. K.; Mandai, A. K. Tetrahedron 1981, 37, 3547.
8. Brown, H. C.; Ayyangar, N. R.; Zweifel, G. J. Am. Chem. Soc. 1964, 86, 397.
9. Brown, H. C.; Yoon, N. M. Isr. J. Chem. 1977, 15, 12.
10. Brown, H. C.; Desai, M. C.; Jadhav, P. K. J. Org. Chem., preceding paper in this issue.
11. Rüttimann, A.; Mayer, H. Helv. Chim. Acta 1980, 63, 1456.
12. Brown, H. C.; Ayyangar, N. R.; Zweifel, G. J. Am. Chem. Soc. 1964, 86, 1071.
13. Brown, H. C.; Yoon, N. M. J. Am. Chem. Soc. 1977, 99, 5514.
14. Brown, H. C.; Mandai, A. K.; Yoon, N. M.; Singaram, B.; Schwier, J. R.; Jadhav, P. K. J. Org. Chem. preceding paper in this issue.
15. Brown, H. C.; Schwier, J. R.; Singaram, B. J. Org. Chem. 1978, 43, 4395.
16. Mandai, A. K.; Jadhav, P. K.; Brown, H. C. J. Org. Chem. 1980, 45, 3543.
17. Brown, H. C.; Jadhav, P. K. J. Org. Chem. 1981, 46, 5047.
18. Brown, H. C.; Negishi, E.; Katz, J.-J. J. Am. Chem. Soc. 1975, 97, 2791.
19. For literature on maximum rotations and absolute configurations of organic compounds, see: Klyne, W.; Buckingham, J. “Atlas of Stereochemistry”; Oxford University Press: New York, 1978.
20. Jacques, J.; Gross, C.; Bourcier, S. In “Fundamentals and Methods of Stereochemistry”; Kagan, H. B., Ed.; Georg Thieme Verlag: Stuttgart, 1977; Vol. 4.