Stereoselective synthesis of sulfinates from mannitol derived sulfites

Tetrahedron Asymmetry

Volumn 7, Issue 4, 1996, Pages 1007-1010

  Pelloux Léon, Nadia ^a   Gautier Luneau, Isabelle ^a   Wendt, Silke ^a   Vallée, Yannick ^a  

^a UNIVERSITÉ JOSEPH FOURIER   (France)

Author keywords

[No Author keywords available]

Indexed keywords

SULFINIC ACID DERIVATIVE;

ARTICLE; CRYSTALLOGRAPHY; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 0029872938     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/0957-4166(96)00104-8     Document Type: Article

References (24)

1. Andersen, K. K. Tetrahedron Lett., 1962, 93-95. Jacobus, J.; Mislow, K. J. Am. Chem. Soc., 1967, 89, 5228-5234. Cherkaoui, M. Z.; Nicoud, J.-F. New J. Chem., 1995, 19, 851-861.
2. Andersen, K. K. Tetrahedron Lett., 1962, 93-95. Jacobus, J.; Mislow, K. J. Am. Chem. Soc., 1967, 89, 5228-5234. Cherkaoui, M. Z.; Nicoud, J.-F. New J. Chem., 1995, 19, 851-861.
3. Andersen, K. K. Tetrahedron Lett., 1962, 93-95. Jacobus, J.; Mislow, K. J. Am. Chem. Soc., 1967, 89, 5228-5234. Cherkaoui, M. Z.; Nicoud, J.-F. New J. Chem., 1995, 19, 851-861.
4. For other ways to sulfoxides, see, inter alia : Solladié, G. Synthesis, 1981, 185-196. Walker, A. J. Tetrahedron: Asymmetry, 1992, 3, 961-998. Fernandez, I.; Khiar, N., Llera, J. M., Alcudia, F. J. Org. Chem., 1992, 57, 6789-6796. Khiar, N.; Fernandez, I.; Alcudia, F. Tetrahedron Lett., 1994, 35, 5719-5722. Nicoud, J. F.; Cherkaoui, M. Z. Tetrahedron: Asymmetry , 1995, 6, 1941-1946. Adam, W.; Mitchell, C. M.; Saha-Möller, C. R. Tetrahedron, 1994, 50, 13121-13124 ; Bulman Page, P.C.; Heer, J. P.; Bethell, D.; Collington, E. W.; Andrews, D. M. Tetrahedron: Asymmetry , 1995, 6, 2911-2914 ; Brunel, J. M.; Diter, P.; Duetsch, M.; Kagan H. B. J. Org. Chem., 1995, 60, 8086-8088.
5. For other ways to sulfoxides, see, inter alia : Solladié, G. Synthesis, 1981, 185-196. Walker, A. J. Tetrahedron: Asymmetry, 1992, 3, 961-998. Fernandez, I.; Khiar, N., Llera, J. M., Alcudia, F. J. Org. Chem., 1992, 57, 6789-6796. Khiar, N.; Fernandez, I.; Alcudia, F. Tetrahedron Lett., 1994, 35, 5719-5722. Nicoud, J. F.; Cherkaoui, M. Z. Tetrahedron: Asymmetry , 1995, 6, 1941-1946. Adam, W.; Mitchell, C. M.; Saha-Möller, C. R. Tetrahedron, 1994, 50, 13121-13124 ; Bulman Page, P.C.; Heer, J. P.; Bethell, D.; Collington, E. W.; Andrews, D. M. Tetrahedron: Asymmetry , 1995, 6, 2911-2914 ; Brunel, J. M.; Diter, P.; Duetsch, M.; Kagan H. B. J. Org. Chem., 1995, 60, 8086-8088.
6. For other ways to sulfoxides, see, inter alia : Solladié, G. Synthesis, 1981, 185-196. Walker, A. J. Tetrahedron: Asymmetry, 1992, 3, 961-998. Fernandez, I.; Khiar, N., Llera, J. M., Alcudia, F. J. Org. Chem., 1992, 57, 6789-6796. Khiar, N.; Fernandez, I.; Alcudia, F. Tetrahedron Lett., 1994, 35, 5719-5722. Nicoud, J. F.; Cherkaoui, M. Z. Tetrahedron: Asymmetry , 1995, 6, 1941-1946. Adam, W.; Mitchell, C. M.; Saha-Möller, C. R. Tetrahedron, 1994, 50, 13121-13124 ; Bulman Page, P.C.; Heer, J. P.; Bethell, D.; Collington, E. W.; Andrews, D. M. Tetrahedron: Asymmetry , 1995, 6, 2911-2914 ; Brunel, J. M.; Diter, P.; Duetsch, M.; Kagan H. B. J. Org. Chem., 1995, 60, 8086-8088.
7. For other ways to sulfoxides, see, inter alia : Solladié, G. Synthesis, 1981, 185-196. Walker, A. J. Tetrahedron: Asymmetry, 1992, 3, 961-998. Fernandez, I.; Khiar, N., Llera, J. M., Alcudia, F. J. Org. Chem., 1992, 57, 6789-6796. Khiar, N.; Fernandez, I.; Alcudia, F. Tetrahedron Lett., 1994, 35, 5719-5722. Nicoud, J. F.; Cherkaoui, M. Z. Tetrahedron: Asymmetry , 1995, 6, 1941-1946. Adam, W.; Mitchell, C. M.; Saha-Möller, C. R. Tetrahedron, 1994, 50, 13121-13124 ; Bulman Page, P.C.; Heer, J. P.; Bethell, D.; Collington, E. W.; Andrews, D. M. Tetrahedron: Asymmetry , 1995, 6, 2911-2914 ; Brunel, J. M.; Diter, P.; Duetsch, M.; Kagan H. B. J. Org. Chem., 1995, 60, 8086-8088.
8. For other ways to sulfoxides, see, inter alia : Solladié, G. Synthesis, 1981, 185-196. Walker, A. J. Tetrahedron: Asymmetry, 1992, 3, 961-998. Fernandez, I.; Khiar, N., Llera, J. M., Alcudia, F. J. Org. Chem., 1992, 57, 6789-6796. Khiar, N.; Fernandez, I.; Alcudia, F. Tetrahedron Lett., 1994, 35, 5719-5722. Nicoud, J. F.; Cherkaoui, M. Z. Tetrahedron: Asymmetry , 1995, 6, 1941-1946. Adam, W.; Mitchell, C. M.; Saha-Möller, C. R. Tetrahedron, 1994, 50, 13121-13124 ; Bulman Page, P.C.; Heer, J. P.; Bethell, D.; Collington, E. W.; Andrews, D. M. Tetrahedron: Asymmetry , 1995, 6, 2911-2914 ; Brunel, J. M.; Diter, P.; Duetsch, M.; Kagan H. B. J. Org. Chem., 1995, 60, 8086-8088.
9. For other ways to sulfoxides, see, inter alia : Solladié, G. Synthesis, 1981, 185-196. Walker, A. J. Tetrahedron: Asymmetry, 1992, 3, 961-998. Fernandez, I.; Khiar, N., Llera, J. M., Alcudia, F. J. Org. Chem., 1992, 57, 6789-6796. Khiar, N.; Fernandez, I.; Alcudia, F. Tetrahedron Lett., 1994, 35, 5719-5722. Nicoud, J. F.; Cherkaoui, M. Z. Tetrahedron: Asymmetry , 1995, 6, 1941-1946. Adam, W.; Mitchell, C. M.; Saha-Möller, C. R. Tetrahedron, 1994, 50, 13121-13124 ; Bulman Page, P.C.; Heer, J. P.; Bethell, D.; Collington, E. W.; Andrews, D. M. Tetrahedron: Asymmetry , 1995, 6, 2911-2914 ; Brunel, J. M.; Diter, P.; Duetsch, M.; Kagan H. B. J. Org. Chem., 1995, 60, 8086-8088.
10. For other ways to sulfoxides, see, inter alia : Solladié, G. Synthesis, 1981, 185-196. Walker, A. J. Tetrahedron: Asymmetry, 1992, 3, 961-998. Fernandez, I.; Khiar, N., Llera, J. M., Alcudia, F. J. Org. Chem., 1992, 57, 6789-6796. Khiar, N.; Fernandez, I.; Alcudia, F. Tetrahedron Lett., 1994, 35, 5719-5722. Nicoud, J. F.; Cherkaoui, M. Z. Tetrahedron: Asymmetry , 1995, 6, 1941-1946. Adam, W.; Mitchell, C. M.; Saha-Möller, C. R. Tetrahedron, 1994, 50, 13121-13124 ; Bulman Page, P.C.; Heer, J. P.; Bethell, D.; Collington, E. W.; Andrews, D. M. Tetrahedron: Asymmetry , 1995, 6, 2911-2914 ; Brunel, J. M.; Diter, P.; Duetsch, M.; Kagan H. B. J. Org. Chem., 1995, 60, 8086-8088.
11. For other ways to sulfoxides, see, inter alia : Solladié, G. Synthesis, 1981, 185-196. Walker, A. J. Tetrahedron: Asymmetry, 1992, 3, 961-998. Fernandez, I.; Khiar, N., Llera, J. M., Alcudia, F. J. Org. Chem., 1992, 57, 6789-6796. Khiar, N.; Fernandez, I.; Alcudia, F. Tetrahedron Lett., 1994, 35, 5719-5722. Nicoud, J. F.; Cherkaoui, M. Z. Tetrahedron: Asymmetry , 1995, 6, 1941-1946. Adam, W.; Mitchell, C. M.; Saha-Möller, C. R. Tetrahedron, 1994, 50, 13121-13124 ; Bulman Page, P.C.; Heer, J. P.; Bethell, D.; Collington, E. W.; Andrews, D. M. Tetrahedron: Asymmetry , 1995, 6, 2911-2914 ; Brunel, J. M.; Diter, P.; Duetsch, M.; Kagan H. B. J. Org. Chem., 1995, 60, 8086-8088.
12. Kagan , H. B.; Rebiere, F.; Samuel, O. Phosporus, Sulfur, Silicon, 1991, 58, 89-110.
13. Rebiere, F.; Samuel, O.; Ricard, L.; Kagan , H. B. J. Org. Chem., 1991, 56, 5991-5999.
14. 4), however with poor stereoselectivities.
15. 2a was previously known : J. J. Brimacombe, M. E. Evens, A. B. Foster and J. M. Weber, J. Am. Chem. Soc., 1964, 2735.
16. 2).
17. 4 and evaporated. The crude product was submitted to column chromatography or crystallized from ether.
18. 3CN mixtures; Shimadzu UV diode array detector.
19. 7 : C: 52.44, H: 8.25, S: 8.75 ; found : C: 52.48, H: 8.36, S: 8.65.
20. 2).
21. 2.
22. The sulfurane shown in Scheme 2 can be regarded either as an intermediate or as a transition state. Concerning possible pseudorotation in sulfurane intermediates, see : Okuyama T., Phosporus, Sulfur, Silicon, 1994, 95-96, 113-125.
23. In order to study the effect of the Lewis acid we have effected control experiments where the Lewis acid was added after the Grignard reagent. In agreement with a kinetic control (and not an equilibration), the observed d.e. were then the same than without Lewis acid.
24. 2).