9-Borabicyclo[3.3.2]decanes and the asymmetric hydroboration of 1,1-disubstituted alkenes

Journal of the American Chemical Society

Volumn 130, Issue 29, 2008, Pages 9218-9219

  Gonzalez, Ana Z ^a   Román, José G ^a   Gonzalez, Eduvigis ^a   Martinez, Judith ^a   Medina, Jesus R ^a   Matos, Karl ^a   Soderquist, John A ^a  

^a UNIVERSITY OF PUERTO RICO   (Puerto Rico)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; DECANE;

ARTICLE; HYDROBORATION;

ALCOHOLS; ALKANES; ALKENES; BORANES; BOROHYDRIDES; MODELS, MOLECULAR; MOLECULAR CONFORMATION; PSEUDOEPHEDRINE; STEREOISOMERISM;

EID: 47749093975     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja803119p     Document Type: Article

References (20)

1. (a) Brown, H. C.; Zweifel, G. J. Am. Chem. Soc. 1961, 83, 486.
2. (b) Zweifel, G.; Ayyangar, R.; Munekata, T.; Brown, H. C. J. Am. Chem. Soc. 1963, 85, 1076.
3. (c) Zaidlewicz, M. in Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon: Oxford, 1982, 7, 229, and references cited therein.
4. (a) Brown, H. C.; Schwier, J. R.; Singaram, B. J. Org. Chem. 1978, 43, 4397.
5. (b) Brown, H. C.; Singaram, B. J. Am. Chem. Soc. 1984, 106, 1797.
6. (c) Brown, H. C.; Jadhav, P. K.; Mandal, A. K. J. Org. Chem. 1978, 43, 5074.
7. (d) Srebnik, M.; Ramachandran, P. V. Aldrichimica Acta 1987, 20, 9.
8. Masamune, S.; Kim, B. M.; Petersen, J. S.; Sato, T.; Veenstra, S. J.; Imai, T. J. Am. Chem. Soc. 1985, 107, 4549.
9. (a) Hayashi, T.; Matsumoto, Y.; Ito, Y. Tetrahedron Asymmetry 1991, 2, 601.
10. (b) Burgess, K.; Ohlmeyer, M. J. Chem. Rev. 1991, 91, 1199.
11. (a) Canales, E.; Prasad, K. G.; Soderquist, J. A. J. Am. Chem. Soc. 2005, 127, 11572.
12. (b) Burgos, C. H.; Canales, E.; Matos, K.; Soderquist, J. A. J. Am. Chem. Soc. 2005, 127, 8044.
13. -1 for the dissociation of (±)-1b dimer. See: (a) Soderquist, J. A.; Matos, K.; Burgos, C. H.; Lai, C.; Vaquer, J.; Medina, J. R. In Contemporary Boron Chemistry; Davidson M. G., Hughes A. K., Marder, T. B., Wade, K., Eds.; Royal Society of Chemistry: Cambridge, U.K., 2000; pp 472-482.
14. (b) Soderquist, J. A.; Matos, K.; Burgos, C. H.; Lai, C.; Vaquer, J.; Medina, J. R.; Huang, S. D. In Organoboranes for Syntheses; Ramachandran, P. V., Brown, H. C., Eds.; ACS Symposium Series 783; American Chemical Society: Washington, D. C., 2000; Chapter 13, pp 176-194.
15. For substrate control, see for example: Evans, D. A.; Fu, G. C.; Hoveyda, A. H. J. Am. Chem. Soc. 1992, 114, 6671.
16. (a) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
17. (b) Suzuki, A. J. Organomet. Chem. 1999, 576, 147.
18. (c) Kotha, S.; Lahiri, K.; Kashinath, D. Tetrahedron 2002, 58, 9633.
19. (d) Danishefsky, S. J.; Chemler, S. R.; Trauner, D. Angew. Chem., Int. Ed. 2001, 40, 4544.
20. No kinetic resolution of diasteromeric 5a was observed with its complete reaction in both processes (e.g., 7g, 7h, 6i: dr = 88:12).