A β-Hydroxyethyl Carbanion Equivalent

Journal of Organic Chemistry

Volumn 62, Issue 11, 1997, Pages 3758-3761

  Klos, Andrew M ^a   Heintzelman, Geoffrey R ^a   Weinreb, Steven M ^a  

^a PENNSYLVANIA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0345231095     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo970226t     Document Type: Article

References (19)

1. Heintzelman, G. R.; Weinreb, S. M. J. Org. Chem. 1996, 61, 4594.
2. For related hydroxymethyl carbanion equivalents, see: (a) Tamao, K.; Ishida, N.; Kumada, M. J. Org. Chem. 1983, 48, 2120. (b) Tamao, K.; Ishida, N. Tetrahedron Lett. 1984, 25, 4245. (c) Tamao, K.; Ishida, N. J. Organomet. Chem. 1984, 269, C37.
3. For related hydroxymethyl carbanion equivalents, see: (a) Tamao, K.; Ishida, N.; Kumada, M. J. Org. Chem. 1983, 48, 2120. (b) Tamao, K.; Ishida, N. Tetrahedron Lett. 1984, 25, 4245. (c) Tamao, K.; Ishida, N. J. Organomet. Chem. 1984, 269, C37.
4. For related hydroxymethyl carbanion equivalents, see: (a) Tamao, K.; Ishida, N.; Kumada, M. J. Org. Chem. 1983, 48, 2120. (b) Tamao, K.; Ishida, N. Tetrahedron Lett. 1984, 25, 4245. (c) Tamao, K.; Ishida, N. J. Organomet. Chem. 1984, 269, C37.
5. For an excellent review of C-Si bond oxidation and lead references see: Jones, G. R.; Landais, Y. Tetrahedron 1996, 52, 7599.
6. Cf. Trost, B. M.; Imi, K.; Davies, I. W. J. Am. Chem. Soc. 1995, 117, 5371.
7. An attempt to form a Grignard reagent from commercially available (2-chloroethyl)triethoxysilane failed.
8. Saigo, K.; Tateishi, K.; Adachi, H.; Saotome, Y. J. Org. Chem. 1988, 53, 1572.
9. Kim, K. S.; Kim, S. J. Song, Y. H.; Hahn, C. S. Synthesis 1987, 1017.
10. Cohen, T.; Jeong, I.-H.; Mudryk, B.; Bhupathy, M.; Awad, M. M. A. J. Org. Chem. 1990, 55, 1528.
11. Gajda, T. Synthesis 1987, 1108.
12. Vigneron, J. P.; Dhaenens, M.; Horeau, A. Tetrahedron 1977, 33, 507.
13. Canonne, P.; Foscolos, G. B.; Belanger, D. J. Org. Chem. 1980, 45, 1828.
14. Portnyagin, Y. M.; Pak, N. E. J. Org. Chem. USSR (Engl. Transl.) 1973, 9, 461.
15. Piers, E.; Oballa, R. M. J. Org. Chem. 1996, 61, 8439.
16. Fetizon, M.; Golfier, M.; Montaufier, M. T.; Rens, J. Tetrahedron 1975, 31, 987.
17. Whitesell, J. K.; Lawrence, R. M.; Chen, H.-H. J. Org. Chem. 1986, 51, 4779.
18. Nair, M. G.; Burke, B. A. Phytochemistry 1988, 27, 3169.
19. The molarity of Grignard reagent 4 can be assayed by standard procedures: Crompton, T. R. In The Chemistry of the Metal-Carbon Bond; Hartley, F. R., Patai, S., Eds.; Wiley: Chichester, 1982; Vol. 1, p 664.