[2,3]-Sigmatropic rearrangement of allylic sulfur ylides derived from trimethylsilyldiazomethane (TMSD)

Tetrahedron Letters

Volumn 40, Issue 50, 1999, Pages 8923-8927

  Aggarwal, Varinder K ^a   Ferrara, Marco ^a   Hainz, Rüdiger ^a   Spey, Sharon E ^a  

^a UNIVERSITY OF SHEFFIELD   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL SULFIDE; DIAZOMETHANE; RHENIUM; SULFUR DERIVATIVE; TRIMETHYLSILYL DERIVATIVE;

ARTICLE; CATALYST; DERIVATIZATION; DIASTEREOISOMER; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0033544787     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01896-1     Document Type: Article

References (19)

1. Padwa, A.; Hornbuckle, S. F. Chem. Rev. 1991, 91, 263-309.
2. Doyle, M. P.; Forbes, D. C. Chem. Rev. 1998, 98, 911-935.
3. Li, A.-H.; Dai, L.-X.; Aggarwal, V. K. Chem. Rev. 1997, 97, 2341-2372.
4. McKervey, M. A.; Ye, T. Chem. Rev. 1994, 94, 1091-1160.
5. Shioiri, T.; Aoyama, T. In Advances in Using Synthons in Organic Chemistry; Dondoni, A., Ed.; JAI Press: London, 1993; Vol. 1, pp. 51-101.
6. Van Vranken, D. L.; Carter, D. S. Tetrahedron Lett. 1999, 40, 1617-1620.
7. Seyferth, D.; Menzel, H.; Dow, A. W.; Flood, T. C. J. Organomet. Chem. 1972, 44, 279-290.
8. Using Co catalysts slow addition does not seem to be required: Fukuda, T.; Irie, R.; Katsuki, T. Tetrahedron 1999, 55, 649-664.
9. All the allylic sulfides were prepared from the corresponding halides by standard procedures. See, for example: Zheng, Y. F.; Dodd, D. S.; Oehlschager, A. C.; Hartman, P. G. Tetrahedron 1995, 51, 5255-5276.
10. 22SSi requires: C, 67.13; H, 8.85).
11. Sulfone was obtained in 94% yield by oxidation with oxone: Trost, B. M.; Curran, D. P. Tetrahedron Lett. 1981, 22, 1287-1290. The authors have deposited atomic coordinates for the sulfone with the Cambridge Crystallographic Data Centre. The coordinates can be obtained on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK.
12. Weinreb, S. M.; Garigipati, R. S.; Cordova, R.; Parvez, M. Tetrahedron 1986, 42, 2979-2983.
13. Kocienski, P.; Todd, M. J. Chem. Soc., Perkin Trans. 1 1983, 1783-1789.
14. Bruckner, R. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 6, pp. 873-908.
15. Chiral Rh, Cu and Co catalysts were tested by van Vranken (Ref. 6) but no comment on the enantioselectivity was provided.
16. Nishibayashi, Y.; Ohe, K.; Uemura, S. J. Chem. Soc., Chem. Commun. 1995, 1245-1246.
17. Doyle, M. P.; Forbes, D. C.; Vasbinder, M. M.; Peterson, C. S. J. Am. Chem. Soc. 1998, 120, 7653-7654.
18. 4]. (equation presented)
19. In contrast, metal-free ylides are believed to be involved in sulfur ylide rearrangements using Co catalysts (Ref. 8) and the similar diastereoselectivity observed with a variety of Cu catalysts (Ref. 16) suggests that metal-free ylides are probably involved with this metal also.