DOI: 10.1039/A701756A
(Paper)
Reference Section for: Chem. Commun., 1997, 941-942
A concise asymmetric synthesis of the pheromone 1-methylcyclohex-2-enol via a ‘merged substitution-elimination reaction’
(Note: The full text of this document is currently only available in the PDF Version )
David P. G. Hamon and Kellie L. Tuck
Abstract
The title compound is prepared (>94% ee) by a three step synthesis from 1-methylcyclohexene via a ‘merged substitution-elimination reaction’ involving a phenylselenide ion.
References
- K. Mori, B. G. Hazra, R. J. Pfeiffer and A. K. Gupta, Tetrahedron, 1987, 43, 2249 CrossRef CAS.
- K. Mori and J. I. J. Ogoche, Liebigs Ann. Chem., 1988, 903 Search PubMed.
- B. D. Johnston, B. Morgan, A. C. Oehlschlager and S. Ramaswamy, Tetrahedron: Asymmetry, 1991, 2, 377 CrossRef CAS.
- P. Ceccherelli, M. Curini, F. Epifano, M. C. Marcotullio and O. Rosati, J. Org. Chem., 1996, 61, 2882 CrossRef CAS.
- D. P. G. Hamon, R. A. Massy-Westropp and J. L. Newton, Tetrahedron: Asymmetry, 1990, 1, 771 CrossRef CAS.
- A. B. Bueno, M. C. Carreno, J. L. G. Ruano and C. Hamdouchi, Tetrahedron: Asymmetry, 1995, 6, 1237 CrossRef CAS.
- B. S. Lindgren, G. Gries, H. D. Pierce and K. Mori, J. Chem. Ecol., 1992, 18, 1201 Search PubMed.
- S. Winstein, D. Darwish and N. J. Holness, J. Am. Chem. Soc., 1956, 78, 2915 CrossRef CAS.
- H. C. Kolb, M. S. VanNieuwenhze and K. B. Sharpless, Chem. Rev., 1994, 94, 2483 CrossRef CAS and footnote 53 therein.
- K. B. Sharpless and R. F. Lauer, J. Am. Chem. Soc., 1973, 95, 2697 CrossRef CAS.
- P. D. Bartlett and R. H. Rosenwald, J. Am. Chem. Soc., 1934, 56, 1900.
- D. J. McLennan, Tetrahedron, 1975, 31, 2999 CrossRef CAS.
- H. Kwart, K. A. Wilk and D. Chatellier, J. Org. Chem., 1983, 48, 756 CrossRef CAS.
- D. P. G. Hamon and R. J. Kennedy, unpublished observations.
- E. L. Eliel, S. H. Wilen and L. N. Mander, in Stereochemistry of Organic Compounds, Wiley, New York, 1994, p. 723 Search PubMed.