Stereochemical control in the synthesis of tetrahydrofurans by cyclisation of diols with [1,2]-phenylsulfanyl migration

Journal of the Chemical Society, Perkin Transactions 1

Volumn , Issue 4, 2000, Pages 533-546

  Aggarwal, Varinder K ^a,b   Eames, Jason ^a,c   Villa, Maŕia Jesús ^a   McIntyre, Sara ^a   Sansbury, Francis H ^a   Warren, Stuart ^a  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

^b UNIVERSITY OF SHEFFIELD   (United Kingdom)

^c QUEEN MARY UNIVERSITY OF LONDON   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ACIDS; ALDEHYDES; BENZENE; CATALYSIS; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL); TOLUENE;

SPIROCYCLIC COMPOUNDS;

STEREOCHEMISTRY;

EID: 0034696023     PISSN: 14704358     EISSN: None     Source Type: Journal    
DOI: 10.1039/a908810e     Document Type: Article

References (34)

1. V. K. Aggarwal, I. Coldham, S. McIntyre and S. Warren, J. Chem. Soc., Perkin Trans. 1, 1991, 451.
2. L. Djakovitch, J. Eames, R. V. H. Jones, S. McIntyre and S. Warren, Tetrahedron Lett., 1995, 36, 1723.
3. (a) F. H. Sansbury and S. Warren, Tetrahedron Lett., 1991, 32, 3425;
4. (b) S. McIntyre, F. H. Sansbury and S. Warren, Tetrahedron Lett., 1991, 32, 5409;
5. (c) F. H. Sansbury and S. Warren, Tetrahedron Lett., 1992, 33, 539.
6. I. Coldham and S. Warren, J. Chem. Soc., Perkin Trans. 1, 1993, 1637.
7. J. Eames, R. V. H. Jones and S. Warren, Tetrahedron Lett., 1996, 37, 707.
8. K. Chibale and S. Warren, J. Chem. Soc., Perkin Trans. 1, 1995, 2411.
9. J. Eames, M. A. de Ias Heras and S. Warren, Tetrahedron Lett., 1996, 37, 4581.
10. R. C. Hartley, I. C. Richards and S. Warren, J. Chem. Soc., Perkin Trans. 1, 1994, 359.
11. J. E. Baldwin, J. Chem. Soc., Chem. Commun., 1976, 734.
12. A. J. Kirby, Adv. Phys. Org. Chem., 1981, 17, 183.
13. L. Mandolini, Adv. Phys. Org. Chem., 1986, 22, 1.
14. A. de. Groot and B. J. M. Jannsen, Synthesis, 1985, 434.
15. A. de Groot and B. J. M. Jannsen, Tetrahedron Lett., 1981, 22, 887.
16. S. M. Tuladhar and A. G. Fallis, Tetrahedron Lett., 1987, 28, 523.
17. (a) C. H. Heathcock, C. T. Buse, W. A. Kleschick, M. C. Pirrung, J. E. Sohn and J. Lampe, J. Org. Chem., 1980, 45, 1066;
18. (b) C. H. Heathcock, M. C. Pirrung, S. H. Montgomery and J. Lampe, Tetrahedron, 1981, 37, 4087.
19. The two substituents at C(2) of the enolate are assigned relative priorities as normal using the Cahn-Ingold-Prelog rules. For C(I), the highest priority is always given to "O-metal", irrespective of the other substituent. For further details see G. Procter, in Asymmetric Synthesis, Oxford Science Publications, Oxford University Press, 1996, p. 71.
20. M. Hirama, D. S. Garvey, L. D. L. Lu and S. Masamune, Tetrahedron Lett., 1979, 3937.
21. J. Eames, M. A. de las Heras, R. V. H. Jones and S. Warren, Tetrahedron Lett., 1996, 37, 1117.
22. M. Chérest, H. Felkin and N. Prudent, Tetrahedron Lett., 1968, 2199.
23. P. Brownbridge, E. Egert, P. G. Hunt, O. Kennard and S. Warren, J. Chem. Soc., Perkin Trans. 1, 1981, 2751.
24. (a) P. Fellman and J. E. Dubois, Tetrahedron, 1978, 34, 1349;
25. (b) J. E. Dubois and P. Fellman, Tetrahedron Lett., 1975, 1225.
26. V. K. Aggarwal, I. Coldham, S. McIntye, F. H. Sansbury, M.-J. Villa and S. Warren, Tetrahedron Lett., 1988, 29, 4885.
27. P. G. Sammes and D. J. Weller, Synthesis, 1995, 1205.
28. J. Eames and S. Warren, Tetrahedron Lett., 1996,37, 3525.
29. D. R. Williams, J. G. Phillips and B. A. Barner, J. Am. Chem. Soc., 1981, 103, 7398.
30. M. Gruttadauria, P. L. Meo and R. Noto, Tetrahedron, 1999, 55, 4792.
31. S. Yamago, D. Machii and E. Nakamura, J. Org. Chem., 1991, 56, 2098.
32. P. Blatcher and S. Warren, J. Chem. Soc., Perkin Trans. 1, 1985, 1055.
33. H. O. House, L. J. Czuba, M. Gall and H. D. Olmstead, J. Org. Chem., 1969, 34, 2324.
34. H. J. Bestmann and J. Angerer, Justus Liebigs Ann. Chem., 1974, 12, 2085.