The scope and limitation of the [1,4]-SPh shift in the synthesis of allylic alcohols

Journal of the Chemical Society, Perkin Transactions 1

Volumn , Issue 24, 2000, Pages 4456-4461

  Aggarwal, Varinder K ^a,b   Eames, Jason ^a,c   De Las Heras, Maria A ^a   McIntyre, Sara ^a   Warren, Stuart ^a  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

^b UNIVERSITY OF BRISTOL   (United Kingdom)

^c QUEEN MARY UNIVERSITY OF LONDON   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDES; CATALYSIS; SALTS; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL); TOLUENE;

ALLYLIC ALCOHOLS;

ALCOHOLS;

EID: 0034700687     PISSN: 14704358     EISSN: None     Source Type: Journal    
DOI: 10.1039/b005349j     Document Type: Article

References (25)

1. E. L. Eliel, W. H. Pearson, L. M. Jewell and A. G. Abatjoglou, Tetrahedron Lett., 1980, 21, 331.
2. J. Eames, N. Kuhnert, F. H. Sansbury and S. Warren, Synlett, 1999, 1211.
3. M.-J. Villa and S. Warren, J. Chem. Soc., Perkin Trans. 1, 1994, 2954.
4. J. Eames, N. Kuhnert and S. Warren, Synlett, 1999, 1215.
5. (a) L. Djakovitch, J. Eames, R. V. H. Jones, S. McIntyre and S. Warren, Tetrahedron Lett., 1995, 36, 1723;
6. (b) L. Djakovitch, J. Eames, D. J. Fox, F. H. Sansbury and S. Warren, J. Chem. Soc., Perkin Trans. 1, 1999, 2771.
7. Preliminary communication: J. Eames, M. A. de las Heras, R. V. H. Jones and S. Warren, Tetrahedron Lett., 1996, 37, 1117.
8. (a) A. J. Kirby, Adv. Phys. Org. Chem., 1981, 17, 183;
9. (b) L. Mandolini, Adv. Phys. Org. Chem., 1986, 22, 1.
10. What is exo- to the sulfonium ring in the spirocyclic intermediate 13 is endo- to the cyclohexyl ring and vice versa.
11. (a) V. K. Aggarwal, I. Coldham, S. McIntyre and S. Warren, J. Chem. Soc., Perkin Trans. 1, 1991, 451;
12. (b) V. K. Aggarwal, J. Eames, M.-J. Villa, S. McIntyre, F. H. Sansbury and S. Warren, J. Chem. Soc., Perkin Trans. 1, 2000, 533.
13. M. S. Wadia, R. S. Mali, S. G. Tilve and V. J. Yadav, Synthesis, 1987, 401.
14. M. Hannaby, P. Judson and S. Warren, J. Chem. Soc., Perkin Trans. 1, 1992, 2609.
15. E. L. Eliel, R. O. Hutchins, R. Mebane and R. L. Willer, J. Org. Chem., 1976, 41, 1052.
16. J. Eames, D. J. Fox, M. A. de la Heras and S. Warren, J. Chem. Soc., Perkin Trans. 1, 2000, 1903.
17. S. McIntyre, F. H. Sansbury and S. Warren, Tetrahedron Lett., 1991, 32, 5409.
18. (a) A. de Groot and B. J. M. Jansen, Tetrahedron Lett., 1981, 22, 887;
19. A. de Groot and B. J. M. Jansen, Synthesis, 1985, 434;
20. (b) J. Otera, Synthesis, 1988, 95.
21. C. H. Heathcock, M. C. Pirrung and J. E. Sohn, J. Org. Chem., 1979, 44, 4294.
22. (a) M. Chérest, H. Felkin and N. Prudent, Tetrahedron Lett., 1968, 2199;
23. (b) N. T. Anh and O. Eisenstein, Nouv. J. Chim., 1977, 1, 77.
24. 2SPh signal in the rearranged chloride within the proton NMR spectrum.
25. P. Brownbridge, P. K. G. Hodgson, R. Shepherd and S. Warren, J. Chem. Soc., Perkin Trans. 1, 1976, 2024.