Preparation of alcohols from alkenes via the homologation of boronates with (trimethylsilyl)diazomethane

Organic Letters

Volumn 2, Issue 10, 2000, Pages 1455-1456

  Goddard, Jean Philippe ^a   Le Gall, Thierry ^a   Mioskowski, Charles ^a  

^a CEA SACLAY   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0038743633     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol005780v     Document Type: Article

References (20)

1. Brown, H. C.; Hubbard, J. L.; Smith, K. Synthesis 1979, 701.
2. For reviews, see: (a) Pelter, A.; Smith, K.; Brown, H. C. Borane Reagents; Academic Press: London, 1988.
3. (b) Vaultier, M.; Carboni, B. In Comprehensive Organometallic Chemistry; Abel, E. W., Stone, F. G. A., Wilkinson, G., McKillop, A., Eds.; Pergamon: Oxford, 1995: Vol. 11, pp 191-276.
4. Tufariello, J. J.; Lee, L. T. C. J. Am. Chem. Soc. 1966, 88, 4757.
5. Tufariello, J. J.; Wojtkowski, P.; Lee, L. T. C. Chem. Commun. 1967, 505.
6. (a) Meerwein, H.; Hinz, G. Liebigs Ann. Chem. 1930, 484, 1.
7. (b) Bawn, C. E. H.; Ledwith, A. Prog. Boron Chem. 1964, 1, 345 and references therein.
8. Shea, K. J.; Walker, J. W.; Zhu, H.; Paz, M.; Greaves, J. J. Am. Chem. Soc. 1997, 119, 9049.
9. (a) Sadhu, K. M.; Matteson, D. S. Organometallics 1985, 4, 1687.
10. (b) Michnick, T. J.; Matteson, D. S. Synlett 1991, 631.
11. (a) Brown, H. C.; Singh, S. M.; Rangaishenvi, M. V. J. Org. Chem. 1986, 51, 3150.
12. (b) Brown, H. C.; Singh, S. M. Organometallics 1986, 5, 994.
13. Larson, G. L.; Argüelles, R.; Rosario, O.; Sandoval, S. J. Organomet. Chem. 1980, 198, 15.
14. (a) Matteson, D. S.; Majumbar, D. J. Organomet. Chem. 1980, 184, C41.
15. (b) Matteson, D. S; Majumbar, D. Organometallics 1983, 2, 230.
16. (c) Tsai, D. J. S.; Matteson, D. S. Organometallics 1983, 2, 236.
17. For reviews, see: (a) Shioiri, T.; Aoyama, T. In Encyclopedia of Reagents for Organic Synthesis; Paquette, L. A., Ed.; John Wiley and Sons: Chichester, 1995; Vol. 7, pp 5248-5251.
18. (b) Anderson, R.; Anderson, S. B. In Advances in Silicon Chemistry; Larson, G. L., Ed.; Jai Press: London, 1991; Vol. 1, pp 303-325.
19. The preparation of 10-trimethylsilyl-9-borabicyclo[3.3.2]decane by reaction of (trimethylsilyl)diazomethane with B-methoxy-9-BBN followed by reduction has been reported: Soderquist, J. A.; Matos, K.; Vaquer, J.; Huang, S. D. Book of Abstracts, 214th National Meeting of the American Chemical Society, Las Vegas, NV, September 7-11, 1997; American Chemical Society: Washington, DC, 1997; ORGN-055.
20. Brown, H. C.; Gupta, S. K. J. Am. Chem. Soc. 1975, 97, 5249.