[2,3]-Wittig rearrangements of (trimethylsilyl)methyl allyl ethers

Tetrahedron Letters

Volumn 37, Issue 14, 1996, Pages 2403-2404

  Mulzer, Johann ^a   List, Benjamin ^a  

^a GOETHE UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ETHER DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0029923908     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00321-8     Document Type: Article

References (19)

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2. b) Brückner, R. in Comprehensive Organic Synthesis: Winterfeld, E., Ed; Pergamon Press: Oxford, 1991; Vol.6; pp 873-908.
3. c) Nakai, T., Mikami, K. Chem. Rev. 1986, 86, 885.
4. d) Mikami, K., Nakai, T.; Synthesis 1991, 594.
5. e) Kallmerten, J., Houben-Weyl, Methods of Organic Chemistry, Helmchen, G.; Hoffmann, R.W.; Mulzer, J.; Schaumann, R., ed.; Vol.E21d; pp 3757-3869, Thieme: Stuttgart, 1995.
6. Still, W.C., Mitra, A. J. Am. Chem. Soc. 1978, 100, 1927-1928.
7. Peterson, D.J. J. Org. Chem. 1968, 33, 780. Carey, F.A., ; Court, S. Ibid 1972, 37, 939.
8. Peterson, D.J. J. Org. Chem. 1968, 33, 780. Carey, F.A., ; Court, S. Ibid 1972, 37, 939.
9. Magnus, P.; Roy, G. Organometallics 1982, 1, 553-559.
10. Baum, K.; Lerdal, D.A.; Horn, J.S. J. Org. Chem. 1978, 43, 203-209. Gately, D.A.; Luther, T.A.; Norton, J.R.; Miller, M.M.; Anderson, O.P. J. Org. Chem. 1992, 57, 6496-6502. For typical side reactions under Williamson synthesis conditions, see: Sans, E.A.; Schechter, H. Tetrahedron Lett. 1985, 26, 1119-1122. Chakraborty, T.K.; Reddy, G.V.; J. Chem. Soc., Chem. Commun. 1989, 251.
11. Baum, K.; Lerdal, D.A.; Horn, J.S. J. Org. Chem. 1978, 43, 203-209. Gately, D.A.; Luther, T.A.; Norton, J.R.; Miller, M.M.; Anderson, O.P. J. Org. Chem. 1992, 57, 6496-6502. For typical side reactions under Williamson synthesis conditions, see: Sans, E.A.; Schechter, H. Tetrahedron Lett. 1985, 26, 1119-1122. Chakraborty, T.K.; Reddy, G.V.; J. Chem. Soc., Chem. Commun. 1989, 251.
12. Baum, K.; Lerdal, D.A.; Horn, J.S. J. Org. Chem. 1978, 43, 203-209. Gately, D.A.; Luther, T.A.; Norton, J.R.; Miller, M.M.; Anderson, O.P. J. Org. Chem. 1992, 57, 6496-6502. For typical side reactions under Williamson synthesis conditions, see: Sans, E.A.; Schechter, H. Tetrahedron Lett. 1985, 26, 1119-1122. Chakraborty, T.K.; Reddy, G.V.; J. Chem. Soc., Chem. Commun. 1989, 251.
13. Baum, K.; Lerdal, D.A.; Horn, J.S. J. Org. Chem. 1978, 43, 203-209. Gately, D.A.; Luther, T.A.; Norton, J.R.; Miller, M.M.; Anderson, O.P. J. Org. Chem. 1992, 57, 6496-6502. For typical side reactions under Williamson synthesis conditions, see: Sans, E.A.; Schechter, H. Tetrahedron Lett. 1985, 26, 1119-1122. Chakraborty, T.K.; Reddy, G.V.; J. Chem. Soc., Chem. Commun. 1989, 251.
14. 3) of 6: δ = -3.2, 20.7, 26.0, 27.4, 30.4, 41.1, 63.0, 78.9, 108.4, 123.9, 134.9, 149.8ppm.
15. 3) of 7: δ = 17.5, 19.4, 22.4, 25.5, 37.1, 42.2, 70.0, 114.5, 124.5, 131.3, 143.9ppm.
16. 4, filtration, evaporation and column chromatography (10% EtOAc/hexane) on silica gel, 104mg (0.620mmol, 88%; 95% according to consumed geraniol) of 9 along with 9mg (0.056mmol, 8%) of geraniol were isolated.
17. Wu, Y.-D., Houk, K.N., Marshall, J.A. J. Org. Chem. 1990, 55, 1421-1423.
18. Still, W.C. J. Am. Chem. Soc. 1978, 100, 1481-7. Seitz, D.E., Caroll, J.J., Cataya M., C.P., Lee, S.-H., Zapata, A. Synthetic Commun. 1983, 13, 129-34.
19. Still, W.C. J. Am. Chem. Soc. 1978, 100, 1481-7. Seitz, D.E., Caroll, J.J., Cataya M., C.P., Lee, S.-H., Zapata, A. Synthetic Commun. 1983, 13, 129-34.