Dilongifolylborane: A New Effective Chiral Hydroborating Agent with Intermediate Steric Requirements

Journal of Organic Chemistry

Volumn 46, Issue 14, 1981, Pages 2988-2990

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

^a PURDUE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001507831     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00327a036     Document Type: Article

References (15)

1. Brown, H. C.; Zweifel, G. J. Am. Chem. Soc. 1961, 83, 486.
2. Brown, H. C.; Ayyangar, N. R.; Zweifel, G. J. Am. Chem. Soc. 1964, 86, 397.
3. Brown, H. C.; Yoon, N. M. J. Am. Chem. Soc. 1977, 99, 5514.
4. Brown, H. C.; Schwier, J. R.; Singaram, B. J. Org. Chem. 1978,43, 4395.
5. Brown, H. C.; Yoon, N. M. Isr. J. Chem. 1977,15, 12.
6. Brown, H. C.; Ayyangar, N. R.; Zweifel, G. J. Am. Chem. Soc. 1964, 86, 1071.
7. Mandal, A. K.; Jadhav, P. K.; Brown, H. C. J. Org. Chem. 1980, 45, 3543.
8. Mandal, A. K.; Yoon, N. M. J. Organomet. Chem. 1978,156,183.
9. Lhomme, J.; Ourisson, G. Tetrahedron 1968, 24, 3167.
10. The endo epimer of longifolol, isolongifolol, is prepared by reduction of isolongifolic acid.11
11. Nayak, U. R.; Dev, S. Tetrahedron 1963,19, 2293.
12. In one of the experiments, longifolene was treated with BH3-SMe2 in a 3:1 ratio, but no trialkylborane formation (u B NMR) was observed.
13. For handling of air-and moisture-sensitive compounds, see: Brown, H. C.; Kramer, G. W.; Levy, A. B.; Midland, H. M., Eds. “Organic Syntheses via Boranes”, Wiley-Interscience: New York, 1975; p 191.
14. We are indebted to Dr. U. R. Nayak and Dr. H. R. Sonawane of the National Chemical Laboratory, Poona, India, and to Dr. S. N. Mehra of the Camphor and Allied Products, Bareilly, India, for generous gifts of (+)-longifolene.
15. Postdoctoral Research Associate on Grant 2R01 GM 10937-14 from the National Institutes of Health.