Asymmetric Allylboration with B-Allyl-2-(trimethylsilyl)borolane

Journal of the American Chemical Society

Volumn 111, Issue 5, 1989, Pages 1892-1894

  Short, Robert P ^a   Masamune, Satoru ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0008205773     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00187a061     Document Type: Article

References (11)

1. Mislow, K.; Siegel, J. J. Am. Chem. Soc. 1984, 106, 3319.
2. (a) Braun, M. Angew. Chem., Int. Ed. Engl. 1987, 26, 24 and references cited therein. (b) Masamune, S.; Sato, T.; Kim, B. M.; Wollmann, T. A. J. Am. Chem. Soc. 1986, 108, 8279.
3. (a) Herold, T.; Hoffmann, R. W. Angew. Chem., Int. Ed. Engl. 1978, 17, 768. (b) Hoffmann, R. W. Pure Appl. Chem. 1988, 60, 123. (c) Brown, H. C.; Jadhav, P. K. J. Am. Chem. Soc. 1983, 105, 2092. (d) Jadhav, P. K.; Bhat, K. S.; Perumal, P. T.; Brown, H. C. J. Org. Chem. 1986, 51, 432. (e) Roush, W. R.; Walts, A. E.; Hoong, L. K. J. Am. Chem. Soc. 1985, 107, 8186. (f) Roush, W. R.; Banfi, L. J. Am. Chem. Soc. 1988, 110, 3979.
4. (a) Masamune, S.; Choy, W.; Petersen, J. S.; Sita, L. R. Angew. Chem., Int. Ed. Engl. 1985, 24, 1. For studies on double asymmetric allylboration, see: (b) Roush, W. R.; Palkowitz, A. D.; Palmer, M. A. J. J. Org. Chem. 1987, 52, 316. (c) Roush, W. R.; Palkowitz, A. D. J. Am. Chem. Soc. 1987, 109, 953. (d) Brown, H. C.; Bhat, K. S.; Randad, R. S. J. Org. Chem. 1987, 52, 319.
5. Masamune, S. In Stereochemistry of Organic and Bioorganic Transformations, Bartmann, W., Sharpless, K. B., Eds.; VCH: 1986; p 49.
6. 9
7. Ishii, T.; Kawamura, N.; Matsubara, S.; Utimoto, K.; Kozima, S.; Hitomi, T. J. Org. Chem. 1987, 52, 4416.
8. Brown, H. C.; Negishi, E. Tetrahedron 1977, 33, 2331. For a discussion of the directing effect of silicon in the hydroboration of vinylsilanes, see: Soderquist, J. A.; Brown, H. C. J. Org. Chem. 1980, 45, 3571.
9. Walker, N.; Stuart, D. Acta Crystallogr., Sect. A: Found. Crystallogr. 1983, A39, 158.
10. (a) Short, R. P.; Masamune, S. Tetrahedron Lett. 1987, 28, 2841. Garcia, J.; Kim, B. M.; Masamune, S. J. Org. Chem. 1987, 52, 4831.
11. Reetz, M. T.; Hullmann, M.; Massa, W.; Berger, S.; Rademacher, P.; Heymanns, P. J. Am. Chem. Soc. 1986, 108, 2405.