Design of sulfides with a locked conformation as promoters of catalytic and asymmetric sulfonium ylide epoxidation

Journal of Organic Chemistry

Volumn 70, Issue 10, 2005, Pages 4166-4169

  Davoust, Marion ^a   Brière, Jean François ^a   Jaffrès, Paul Alain ^a   Metzner, Patrick ^a  

^a UNIVERSITÉ DE CAEN   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; COMPUTATIONAL METHODS; DERIVATIVES; OXIDES; SULFUR; SYNTHESIS (CHEMICAL);

CONFORMATION; SULFIDES; SULFONIUM YEILDS; SULFUR DERIVATIVES;

CATALYSIS;

STILBENE OXIDE; SULFIDE; SULFONIUM DERIVATIVE; SULFUR DERIVATIVE;

AB INITIO CALCULATION; ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CHIRALITY; CONFORMATION; ENANTIOMER; EPOXIDATION;

EID: 18744373347     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0479260     Document Type: Article

References (36)

1. For a recent review, see: Aggarwal, V. K.; Winn, C. L. Acc. Chem. Res. 2004, 8, 611-620.
2. For recent contributions on getting insight in the reaction mechanisms, see: (a) Silva, M. A.; Bellenie, B. R.; Goodman, J. M. Org. Lett. 2004, 6, 2559-2562.
3. (b) Aggarwal, V. K.; Richardson, J. Chem. Commun. 2003, 2644-2651.
4. (c) Aggarwal, V. K.; Harvey, J. N.; Richardson, J. J. Am. Chem. Soc. 2002, 124, 5747-5756.
5. (a) Aggarwal, V. K.; Imhyuck, B.; Leeb, H.-Y. Tetrahedron 2004, 60, 9725.
6. (b) Lupattelli, P.; Bonini, C.; Caruso, L.; Gambacorta, A. J. Org. Chem. 2003, 68, 3360-3362.
7. (c) Solladié-Cavallo, A.; Diep-Vohuule, A. J. Org. Chem. 1995, 60, 3494-3498.
8. For recent chiral sulfur reagents promoting bis-arylepoxides synthesis, see: (a) Minière, S.; Reboul, V.; Metzner, P.; Fochi, M.; Bonini, B. F. Tetrahedron: Asymmetry 2004, 15, 3275-3280.
9. (b) Saito, T.; Akiba, D.; Sakairi, M.; Ishikawa, K.; Otani, T. Arkivoc 2004, (ii), 152-171.
10. (c) Ishizaki, M.; Hoshino, O. Chirality 2003, 15, 300-305.
11. (d) Aggarwal, V. K.; Angelaud, R.; Bihan, D.; Blackburn, P.; Fieldhouse, R.; Fonquerna, S. J.; Ford, G. D.; Hynd, G.; Jones, E.; Jones, R. V. H.; Jubault, P.; Palmer, M. J.; Ratcliffe, P. D. J. Chem. Soc., Perkin Trans. 1 2001, 2604-2622. This last reference describes an impressive piece of work toward the elaboration of chiral sulfur derivatives.
12. For efficient stoichiometric approaches as alternatives, see: (a) Aggarwal, V. K.; Bae, I.; Lee, H.-Y.; Richardson, J.; Williams, D. T. Angew. Chem., Int. Ed. 2003, 43, 3274-3278.
13. (b) Solladié-Cavallo, A.; Roje, M.; Isarno, T.; Sunjic, V.; Vinkovic, V. Eur. J. Org. Chem. 2000, 1077-1080.
14. (a) Aggarwal, V. K.; Alonso, E.; Bae, I.; Hynd, G.; Lydon, K. M.; Palmer, M. J.; Patel, M.; Porcelloni, M.; Richardson, J.; Stenson, R. A.; Studley, J. R.; Vasse, J.-L.; Winn, C. L. J. Am. Chem. Soc. 2003, 125, 10926-10940.
15. (b) Winn, C. L.; Bellenie, B. R.; Goodman, J. M. Tetrahedron Lett. 2002, 43, 5427-5430.
16. (c) Zanardi, J.; Leriverend, C.; Aubert, D.; Julienne, K.; Metzner, P. J. Org. Chem. 2001, 66, 5620-5623.
17. Furukawa, N.; Sugihara, Y.; Fujihara, H. J. Org. Chem. 1989, 54, 4222-4224.
18. 2-symmetrical sulfides, see: Breau, L.; Ogilvie, W. W.; Durst, T. Tetrahedron Lett. 1990, 31, 35-38.
19. For an intramolecular version: Kim, H.-H.; Metobo, S.; Jimenez, L. S. Phosphorus, Sulfur, Silicon 2001, 176, 29-47.
20. A lack of reactivity of the sulfur derivatives, due to the presence electron-withdrawing groups nearby, can also be detrimental to the reaction rate; see: Durst, T. Phosphorus, Sulfur Silicon Relat. Elem. 1993, 74, 215-232.
21. 2,5-Dialkylthiolanes are synthesized in two steps from the commercially available chiral 1,4-diols, which are available in bulk from JFC-Juelich Fine Chemicals GmbH Co.: Haberland, J.; Hummel, W.; Daussmann, T.; Liese, A. Org. Proc. Res. Dev. 2002, 6, 458-462.
22. A recent review on organocatalysis including sulfur ylides, see: Dalko, P. I.; Moisan, L. Angew. Chem., Int. Ed. 2004, 43, 5138-5175.
23. For computer-assisted modelisation of chiral sulfur reagents, see: (a) Aggarwal, V. K.; Charmant, J. P. H.; Dudin, L.; Porcelloni, M.; Richardson, J. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5467-5471.
24. (b) Myllymäki, V. T.; Lindvall, M. K.; Koskinen, A. M. P. Tetrahedron 2001, 57, 4629-4635. The described chiral sulfide, in this latter paper, allowed the synthesis of trans-stilbene oxide with 95:5 er, but in poor yield.
25. For an excellent review on chiral phospholanes describing the use of diol precursors, see: Clark, P. C.; Landis, C. R. Tetrahedron: Asymmetry 2004, 15, 2123-2137.
26. (a) Yan, Y.-Y.; RajanBabu, T. V. J. Org. Chem. 2000, 65, 900-906.
27. (b) Li, W.; Zhang, X. J. Org. Chem. 2000, 65, 5871-5874.
28. Dai already described that 20% of a camphor-derived sulfide allowed stilbene oxide synthesis within a day without the need of any transition metal but a maximum of 80:20 er was obtained; see: Li, A.-H.; Dai, L.-X.; Hou, X.-L.; Huang, Y.-Z.; Li, F.-W. J. Org. Chem. 1996, 61, 489-493.
29. It was found that a complete and reproducible conversion occurred in 24 h when distilled benzaldehyde was stabilized with a small amount of catechol. Although catechol is a well-known antioxidant of aldehydes, such behavior in our process is not completely understood. Moreover, this effect was aldehyde dependent. For instance, no difference was observed with 2-naphthaldehyde whatever catechol was used or not.
30. Julienne, K.; Metzner, P.; Henryon, V. J. Chem. Soc., Perkin Trans. 1 1999, 731-735.
31. 4 has been used as PTC for sulfur ylide epoxidation in a racemic approach, see: Solladié-Cavallo, A.; Lupattelli, P.; Marsol, C.; Isarno, T.; Bonini, C.; Caruso, L.; Maiorella, A. Eur. J. Org. Chem. 2002, 1439-1444.
32. 2-, in basic conditions, to perform a counterion exchange with the sulfonium bromide cannot be ruled out, as has been also suggested by a reviewer. This exchange would promote the nonreversible formation of the sulfonium salt due to the non-nucleophilic caracter of the sulfate anions. The ammonium ion would facilitate the sulfate anion extraction from the aqueous phase.
33. 1H NMR even after 24 h; see the Supporting Information.
34. For computational convenience, we replaced the gem-dimethyl group present on the acetal bridge of the sulfonium ylides 8 and 9 by a methylene group, given the lack of influence expected on the conformations.
35. For discussion of such a computational method for sulfonium ylides, see: Lindvall, M. K.; Koskinen, A. M. P. J. Org. Chem. 1988, 64, 4596-4606.
36. Under our conditions no epoxide was obtained from 3-pyridyl carboxaldehyde. 2-Thienyl carboxaldehyde underwent epoxidation in 20% yield after 3 days of reaction.